


Shopping for Love

by samwisewinchester



Series: Shopping 'Verse! [1]
Category: Supernatural
Genre: Alternate Universe - Modern Setting, Angst and Humor, Angst with a Happy Ending, Attempt at Humor, Awkward Flirting, Awkwardness, Bad Flirting, Castiel is a Sweetheart, Depressed Dean Winchester, Destiel - Freeform, Double Dating, Feelings, Flirting, Fluff, Fluff and Angst, Gabriel is a Novak, Grocery Store, Human Castiel, Human Gabriel, I'm trying okay, Internal Monologue, John Winchester's A+ Parenting, Light Angst, M/M, Miscommunication, Misunderstandings, POV Sam Winchester, Relationship Advice, Sabriel - Freeform, Sexual Tension, Tension, Tooth-Rotting Fluff, kind of slow burn?
Language: English
Status: Completed
Published: 2018-02-06
Updated: 2018-05-19
Packaged: 2019-03-14 17:49:11
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 9
Words: 20,088
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13595205
Author URL: https://archiveofourown.org/users/samwisewinchester/pseuds/samwisewinchester
Summary: Sam Winchester is working his way through college as a cashier at a supermarket. Fun stuff, he knows. One day, a dorky guy comes in and decides to ask Sam for advice on how to woo his best friend into being his boyfriend. (Of course, Sam doesn't know that this guy happens to be the roommate of his somewhat estranged brother, Dean. But what he doesn't know won't hurt him, right?)





	1. Chatty Cassie

**Author's Note:**

> Welcome to my fic! It's sort of like an autobiography, because I'm writing down a bunch of my own experiences, especially as pertaining to working in retail! I've been sooooo happy to read all the comments and see all the hits and kudos, and after some thinking, I'm gonna write two more parts to this story! So if you're interested in reading those as they come out, you can subscribe to me to get updates etc. 
> 
> Also, you can follow my Tumblr, if you'd like! It's drabbles-and-shit.tumblr.com

[](https://imgur.com/fq5hFhl)

"Yes, the diapers are on aisle 24," Sam plasters on his usual smile as the 50-something turns on her heel with a disapproving grimace and stalks towards the baby aisle. Normally, the cougars were all over Sam's jawline, polite smile, and damn good body (maybe there's a reason he works out beyond the health aspect, okay?). But it's June, and June is Pride Month, and Pride Month means all the employees of the grocery store can wear as much gay stuff as they care to. Sam, the raging pansexual he is, has a different rainbow outfit for each day of the week, and some of the more homophobic customers seem to take his self expression as a personal insult. He can't find it in himself to really care, though, especially considering that according to company policy, any and all Pride Month-related complaints are thoroughly ignored by HR.

For such a big league grocery chain, Sam was always both surprised and impressed when he found out all the little ways the stores made effort to support its community. Probably, it was a result of being situated in a college town full of forward thinking (and easily butthurt) millennials. Not that he was complaining; he normally sorted himself into that category, anyway. 

"Sam, come to the service desk; Sam to the service desk." As the store's loudspeakers blare, and Sam irrationally feels his face heat up. It was probably nothing, just his manager wondering something or other, but whenever they used the intercom, it always embarrassed him for some reason. He should have picked up a walkie talkie when he clocked in today, but he had completely forgot. Oh well. He flips off the light at his register and walks the half a damn kilometer over to the other side of the store where the customer service desk is located. 

"Hey, what's up Becky?" he asks as he reaches the almost comical scene of his small customer service manager, Becky Rosen, framed by the huge desk. 

Becky grins up at Sam, towering a full foot above her. "Oh, it's not really much! I just needed someone to take this box up to HR. Could you please take it? It's too heavy for me!" 

Sam sighs. First of all, Becky has been hitting on him ever since he got here, and it's starting to get really old. Plus, this was definitely a job for one of the baggers or something. They literally stand around and talk all day, and here he is, doing their jobs for them! Ever the people pleaser, though, Sam smiles and says, "Of course, no problem. Should I just leave it on Zachariah's desk?"

Becky nods so enthusiastically, Sam worries for a second he accidentally asked her to marry him or something, but his fears are alleviated when she adds, "Yep, they’re labels for his printer! Apparently he ran out twice yesterday, which doesn't really make sense to me. I mean, how many labels is he printing up there? Maybe he makes a lot of m--"

"Okay, I think I'd better get a move on with these!" Sam interrupts, not giving two shits about what their store manager does with his labels. 

Becky continues her constant grin and waves a little as Sam hefts the box and makes his way upstairs. 

The contrasting dull silence of the upper office portion of the grocery store grates on Sam’s nerves, and he finds himself rushing to finish his small task and surround himself yet again with the bustling cacophony of the busy half of the building. He drops the box onto Zachariah’s desk and makes good use of his long legs to get downstairs in record time. 

Back on the ridiculously long stretch between the stairs and the register he is scheduled to work the whole day, Sam notices a customer with a very perplexed expression pacing the ends of a couple aisles. As the conscientious he is, Sam decides to help the man (or woman, he corrects himself, then realizes he’s talking to himself and that he’s probably going crazy). As he approaches, he takes the, for simplicity’s sake, man in. He’s got an oversized, tan trenchcoat on over a simple suit, and it looks suspiciously like his blue tie is on backwards. His tousled hair and disgruntled manner completes the picture, and Sam comes to the conclusion that there is an 85% chance this guy is going through a breakup. 

Walking up from an angle which he is sure puts him in the man’s line of sight (he will never make the mistake of “sneaking up on” a customer again; dear lord, never again), Sam puts his smile back on and says in his best customer service voice, “Is there something I can help you find today?” 

The man still manages to look surprised, but he puts on a bit of a smile (or grimace, depending on how you look at it) of his own and turns around to fully face Sam. “Um, yes,” he starts, and wow his voice is low. Like, ‘How can that be his real voice?’ levels of low. “Where’s the...pie?” 

Sam stifles the laugh that was dangerously close to surfacing from the absurdity of the situation and instead just funnels his amusement into another smile. “It’s in our bakery. I can show you, if you’d like?” It’s company policy to always ask the customer if they want you to walk them to the item that they’re looking for. Of course, normal people will always say no thank you, because it’s so damn awkward. 

“Yes please, that would be greatly appreciated.” Looks like this guy isn’t normal, then. Awesome.

More smiles. “Well, the bakery is just this way.” Sam begins to walk towards the pies, and his brain shuffles through the different smalltalk options he has stored up for situations like this. In the end, he settles on, “So what kind of pie are you looking for?” 

The man, weirdly nervous-looking, glances over at Sam before replying, “Apple pie, I think.”

“Mmm, sticking to the classics. Apple pie was always my brother’s favourite, though he’d eat just about any pie you put in front of him. Just about any food in general, actually!” He laughed a little, thinking fondly about his older brother, Dean. Their dad hadn’t been super thrilled when Sam left for college, and a rift had been formed between him and Dean, but he definitely missed him. He hadn’t actually spoken to him in a couple years, so who knows, maybe he didn’t even like pie anymore. 

Since the customer had chosen to not participate in the conversation, Sam let it settle into a somewhat uncomfortable silence for the remaining half a minute it took them to get to the bakery, choosing to lose himself to reminiscing instead. Finally, they arrive at the pies, and smiling, Sam asks, “Is there anything else I can help you find?” 

The man stops his careful examination of the pies and looks back at Sam, seemingly pondering something. Then he says, “Yes, can you please show me to the beers?” 

Yay, more fun time with chatty Cathy. “Of course!”

It took a few minutes for the man to find his perfect pie, and then they were off again. Back to the smalltalk drawing board. “Pie and beer, now you’re really sounding like my brother. You like cheeseburgers, too?” 

The man smiles sincerely for a second before answering, “Yes, they make me very happy.” 

Sam grins, almost sincerely. “I can relate to that, though I’m really more of a salad guy most of the time.” 

As they reach the beer, Sam sends a silent prayer to Liber that the man will let him get back to work now. The registers were probably overrun at this point, and if he doesn’t hurry back, someone will get on his ass for it. 

“All right, here we go,” he says. “Anything else I can help you with?” 

The man looks nervous again and looks around, as if trying to find an excuse for Sam to stay. Finally, he seems to find some resolve and looks Sam in the eye. “Actually, I was wondering if you could give me some advice on my relationship. Um, I noticed all your Pride clothing, and I don’t really have any gay friends, but I need advice, and you seem nice, so I thought maybe you could help, but if you can’t that’s fine, but I thought I’d ask anyway?”

Wow, that was all one breath. And a question? Yes, a question. Relationship advice. Sam could do that, right? He’s had a few relationships, after all. Advice, yeah. No, wait, no. This isn’t smalltalk. This is non-smalltalk at work, a place where he only does smalltalk. No, no. This is not good. Oh fuck it. 

“Yeah, of course! I don’t have tons of experience, but I’ll give my opinion where I can.” Shit. WHY did he just say that? Sam knows nothing about relationships other than what he’s read in books. He’s in a pre-law program, which he got a full ride to. He’s always been 100% nerd. Maybe his body doesn’t make it seem like it, but he is as dorky as hell and knows a lot of nothing about love. But damn if he isn’t good at faking things. He can do this. 

The man brightens up considerably and stops pretending to look at the beer. “Um, well. I have a roommate, see? And he’s also my best friend. He’s not in college, but I am. Anyway, that doesn’t really matter. It’s just, I really like him a lot. Like, I think I love him? But he’s never shown any interest in guys that I’ve seen. I mean, I’m nonbinary, but I look like a man, so. Yeah. And also, I just made him really mad, and I’m not really sure why or how I can apologize. That’s why I’m here, buying his favorite things to give him and apologize with. I wouldn’t mind just being friends with him, but at the very least, I need to apologize well enough that he’ll forgive me. I’m sorry, I know we’ve never met before, and I definitely shouldn’t be dumping my problems on you like this, but… Well, yes. That’s my problem.” During his shpeel, the man increasingly lost whatever confidence he had found to talk with in the first place, and he now he resembles a humanoid pile of jello.

Sam just smiles, because you know what? This guy is just as lost as he is. Actually, he’s probably a little more so. “It’s no problem, man. Look, I don’t know a lot about relationships, but I can tell you for sure that if this guy isn’t a complete asshole, he’ll accept your apology. You’re buying him pie and beer, for crying out loud! But definitely go slow with him. Just work on getting back to being friends before trying anything else. Who knows, he might be super into you! But yeah, the best you can do for now is to tell him that you’re sorry if you did something to hurt his feelings and ask if he’ll still be your friend. And based on what I’ve seen, you’re pretty good at those sad puppy faces, so maybe throw one of those in for good measure. Capiche?”  
The man smiles again, gaining back the support of his legs and replies, “Yes, I capiche. Thank you very much.”

“It’s no big deal. The next time you drop in for groceries, let me know how it went, okay?”

The man nods, still smiling and picks up a 6-pack of some higher end beer. He pauses for a second, then turns back to face Sam again, sets the beer down on the floor, and thrusts out a hand, “My name is Castiel, by the way. Castiel Novak.” 

Sam grins and shakes Castiel’s hand firmly. “Sam Winchester; it’s good to meet you.”

Castiel’s eyes widen for a second as Sam offers his name, but says nothing more than a goodbye before making his way to checkout. 

Sam follows far enough behind to not make it one of those awkward situations where you say bye to someone and then realize you’re both walking the same way, and when he finally makes it back to the front, he groans. There’s a damn line for the registers. Of course. Lovely.

**Notes for the Chapter:**

> How'd you like the first chapter?? I love feedback, soooo...yeah


	2. Sweet as Shit

**Notes for the Chapter:**

> Oh my lanta, thank you guys so much for the support on this so far!! It literally makes me soooooo happy! Also, I edited the tags, so check 'em if you want. AND I didn't actually proofread this, and I don't have a beta right now (le sigh), so sorry about all the crap.

“Thank you; have a good one.” Sam smiles kindly at the older man as he picks up his five full bags of assorted pre-made frozen pasta and makes his way out. 

Another customer is already placing their groceries haphazardly onto the conveyor belt, so Sam good naturedly calls out, “Hey, how are you doing today?’ as he turns the conveyor on and begins scanning their items. 

He was scheduled to work the ‘15 items or less’ register today, which was one of his favorite things to do here, because most people who went through this lane didn’t really want to talk to him, so he could phase out.

“Hey, I’m doing all right. How are you?” If Sam had a dime for every time he’d heard or said himself that exact same phrase, he’s pretty sure he’d never have to work again.

“I’m doing good,” he bounces back, his back killing him, seven summer reading books to be finished in two weeks, no girl or boyfriend, and generally not doing good. “You find everything all right today?”

“Yeah I did, thanks.” Yeah, sure you did. I saw you walking back and forth around the aisles for well over two hours; I’m sure you weren’t struggling to find anything at all.

“Awesome. Would you like this milk in a bag?” Let’s see, this guy looks younger than 30, so that’s a probable no. Oh, and look, he’s wearing chacos. Definite no.

“Ah, no thanks.”

Okay, time for smalltalk… um… 

The customer beat him to the punch. “I love how they let you guys dress to celebrate pride month!”

“Yeah,” Sam grins. “It’s honestly surprisingly forward thinking for a chain store.”

The customer nods, “I really appreciate it; it makes for a sense of inclusion and community.”

Sam smiles and nods his agreement, and a comfortable silence falls, interrupted only by the beeps of the items being passed over the little laser-thing. Lots of candy. Huh. Uh oh, too much silence. It’s getting a bit uncomfortable. Sam raids the smalltalk banks. “So, you in summer school?” Sam himself doesn’t need summer school, and he takes full advantage of the summer months to work full time and get head starts on all his fall courses. Nerdom is not something to be ashamed of.

“Nah, but my brother is. I’ll be in grad school starting in August.”

“Oh, cool.”

Nope, more silence. Not good. Ummmm…

“So, why all the candy?”

The customer grins and looks up at Sam for a minute. “Let’s call it a controlled addiction.” 

Sam laughs and retorts, “Yeah, like my controlled addiction to fixing my hair? Or is it actually under control?” 

The customer laughs too. “Based on the beautiful quality of that mane of yours, I’d say we’re on about the same level here. But at least your addiction isn’t unhealthy.”  
Sam snorts, “For my body maybe but not my wallet.” With a flourishing toss of his luscious locks, he adds, “Oribe Shampoo for Brilliance & Shine. $50 a bottle.”

With a whistle and an eyebrow raise, the customer remarks, “Your Adonis-like beauty makes sense now.”

Wait, is he hitting on Sam? Holy hell, it’s been so long since someone he could actually be interested in hit on him, he can’t tell any more. Shit. 

Um… 

Fuck, this is hard. This conversation was so okay until now. He’s probably not even hitting on you, moron. Just talk about something. Anything. Scare him off. Stay alone forever. 

“Ha, yeah, sure. And you must be mostly eating To’ak chocolate, if we’re using expensive things as the measure of how attractive we are.” Shit, no. That wasn’t scaring him off; that was continuing the flirtation. Shit. Maybe he won’t know how expensive To’ak is.

“Wow, color me impressed and flattered; you know your high end chocolate.” Why does he have a predatory look in his eye? That’s probably just Sam’s imagination. Almost definitely. 

“I had to research it for a paper back in high school,” Sam gives a nervous laugh. “Um, you can insert your card whenever you’re ready.” 

“Sure thing, TRESemmé,” he winks and finishes paying for his groceries, which incidentally ended up being a jar of Nutella, a loaf of bread, a half gallon of milk, and five bags of candy. 

The receipt prints out and Sam hands it over to the customer with a smile. “Thanks; have a good day.”

Instead of grabbing his bags and running off, the man takes his receipt from Sam’s hand, grabs a pen that was sitting on the counter, and scribbles something down, then hands the receipt back. “In case you get bored later,” he says with a smirk, then scampers off. 

Sam watches him leave before examining the receipt. It has a phone number, the name Gabe, and a heart. Huh. 

Wait.

Does this mean Sam might actually have a chance at finding love?? No, probably not. As attractive as the guy, Gabe, was, it probably wouldn’t work out. 

His head still in the clouds, Sam turns off his register light and wanders over to the time clock to clock the start of his 30-minute lunch break. He then meanders over to the bulk goods aisle to get a dollar’s worth of organic, unroasted almonds, because they’re both delicious and nutritious. Screw the haters. They’re all unhealthy. He’ll outlive them all. Yeah.

Making his way back to the small seating area to sit and eat until his break was over, Sam notices a familiar face: Castiel. He smiles and walked up to them to say hello. 

“Hey, Castiel!” He says as he approaches. Wait, wasn’t work a bad place for non-smalltalk? Why was he doing this? Shit, not again. 

“Oh, hello Sam,” Castiel looks up from the pepperoni they were closely examining, smiles, and Sam remembers that this guy is fine. A little weird, but definitely okay to talk to. 

“Soooo…?” Sam verbally pokes Castiel, finding himself really curious about the guy and their boyfriend problems. It’s been about a week since Castiel first came in, and Sam found himself pondering their situation more than a few times in that period.

Castiel tilts their head and squints their eyes as if they have absolutely no idea what Sam is talking about. As he said, weird.

“With your best friend…?” Sam proffers.

Comprehension dawns, and Castiel smiles a little bashfully. “Ah, sorry. Well, I spoke with him. I did as you said and offered my best apology. He told me to, quote, “Forget about it,” and that was all he said on the matter. Everything has gone back to normal, but I still do not know what I did in the first place to make him so angry.” Castiel finished with a sigh and looked down at the bag of pepperoni in his hand.

“Well, that’s not too bad,” Sam smiles encouragingly. It actually sounded kinda bad. Or at least like this guy is a bit of an emotion-suppressing asshole. “So no luck on the relationship front, then?” 

Castiel shakes his head sadly. “No, and I have no idea how to broach the topic. Or even if I should! He doesn’t have a lot of friends in the first place, because he’s not really good at talking to people. I mean, not in a bad way! He just has trouble getting outside of his comfort zone and actually letting people get to know him, you know? He’s really sweet, and I know that, but usually he only lets people see the rougher side of him, and he doesn’t really open up ever, and most of his friends only know him as this guy that he really isn’t, so I don’t want to jeopardize my relationship with him in case I’m the only person he feels comfortable talking to seriously, and if I make him uncomfortable by telling him I have feelings for him, he might not want to talk to me, either!”

Holy fuck, take a breath, Casanova. “Whoa, calm down, man. It’s all right” Sam fees very sorry for the package of pepperoni, which had gotten very squished during that last sentence. 

Castiel heaves a breath. “Sorry; I just don’t know what to do.”

“You’re good; don’t stress.” Sam has no idea what the fuck to tell them to do, because ya know, he sucks at relationships, but hell if he isn’t invested at this point. “Look, can you tell me honestly that you’re sure he’s straight? And that you’re sure he’s not into you? I mean, does he ever do anything that makes you think maybe he’s interested but just thinks along the same lines as you do, that he doesn’t want to ruin your relationship?”

Castiel seems to mull things over in his mind for a second, then slowly responds, “Well… we do make a lot of extended eye contact. I don’t know if that means anything, though.”

Sam tries very hard to not laugh, because damn, extended eye contact is truly the best way into a man’s heart. “Okay, no, that’s good! Anything else?”

“He seems very uncomfortable when I’m in a state of undress while around him… But I always assumed that was because he knows of my sexuality and is off put by it.” Jesus, one thing Sam knew for certain about his new friend was that the more uncomfortable he got, the more rigid his words got. I mean, who the hell says ‘state of undress,’ or ‘off put’? 

“That could actually be a good sign! Look, don’t push it too hard, but maybe drop some hints here and there? Ask him about relationships or something; I don’t know. But don’t give up yet, Castiel!” Sam uses his most sincere grin, then begins to wonder is maybe he’s a terrible person for only having levels of smiles and laughs instead of actual, real ones… Huh, maybe he should go to therapy or something. It’s probably not healthy. Uh, anyway. 

Castiel squeezes the pepperoni bag once more, then smiles too. “Yes, I’ll keep trying. And I’ll let you know what progress I’ve made, the next time I come into the store.”

Sam glances at his watch and realizes that he has about five minutes left in his break, so he really   
needs to get back to the front of the store, so he claps Castiel encouragingly on the shoulder and says, “Remember, don’t stress too much, Castiel. I’ve really got to get back to work, but I’ll be rooting for you.”

“I will try, and thank you, Sam.” Castiel glances down at the pepperoni for a moment, then looks back up and smiles as he says,“By the way, you can call me Cas.”

Sam grins, “Awesome; I was having a little trouble with your full name, but I guess you could tell.”

They part ways, Cas off to look at more pepperoni, Sam to clock back in. As he walks, he wonders what the hell he’s gotten himself into. I mean, after all, it’s not like he knows anything about this type of stuff (love??), but here he is, giving someone else advice on it. Oh, and he can’t forget about that Gabe guy. And he should really email his dad or brother to find out what the hell is up with them. He doesn’t even know where either of them are living right now. And it’s only a few weeks till the semester starts. And his back hurts. And he’s pretty sure there isn’t any food at his apartment. 

“Hey Sam, how are you doing?” one of his coworkers calls out. 

“I’m great! How are you?” Sam internally sobs and wishes he could be at home, washing his hair.

**Notes for the Chapter:**

> Thoughts? Critiques? Loving words? Also, Happpy Valentines Day, my dudes! <3


	3. Egos and Embarrassment

**Notes for the Chapter:**

> Seriously, thank you guys SO MUCH for all the support on this! It's filling me with such joy; you have no idea. Also, sorry, yet again I was too lazy to proofread this chapter, so ignore all the dumbest parts XD

“I’m sorry, this coupon is expired.” Sam points at the date on the coupon, clearly exposing the fact that it expired almost two years ago. 

“But can’t you take it anyway?” The customer is the classic ‘Can I Speak To Your Manager’ soccer mom, and Sam takes a minute to collect all his self control, because it’s a coupon for 20 cents off. 20 cents. She’s probably going to cause him a lot of trouble. For 20 damn cents. 

“I’m sorry, we can’t accept any out of date coupons, ma’am.” Sam’s customer service smile does wonders, but it can’t perform miracles--it can’t stop the rage of a pissed off soccer mom. 

“Well, the last time I was here, it didn’t matter!” Liiiiies. Unless she went through Ash’s line, no one else would have okayed an expired coupon, either. Ash didn’t really give a shit about much of anything around here, so Sam wouldn’t put it past him to have avoided the whole painful  
situation by just giving her the money straight from his own pocket. 

“I’m very sorry, but it’s against company policy.” Please, please, please, just drop it. Seriously, it’s so not worth it, lady. 

“Can I speak to your manager?” There it is. Sam does not roll his eyes. He is very proud. 

“Yes, of course, ma’am.” Sam picks up his small radio and speaks into it. “Becky, can you come to register four? A customer would like to speak to you.” He then sets the radio back down and looks up at the customer, smiling. “She’ll be here in just a minute.” 

Sometimes Sam wonders if there are genuinely evil people in this world. Of course, he’s always been a firm believer that everyone starts out basically good, and their environments and experiences cause the more long-term, douchey effects shown in their character as adults. 

But damn. Fucking soccer moms. They’re on the same level as the people who talk during movies and the people who don’t use their blinker when turning or changing lanes. They’re all things that are easily avoidable, yield no real benefits, are detrimental to the people surrounding the perpetrator, and are 100% fucking dickish. 

Shit, Sam feels like love for humanity slipping away, and he’s only halfway through his shift for the day. GOOD THOUGHTS. Um, People Are Awesome videos. That one guy that gave you a dollar when your card was declined. Hugh Jackman. Okay, that was a close one, but thanks to the Aussies, another crisis has been averted. 

Becky hops up, and Sam snaps back to reality. “What can I do for you?” she politely asks the soccer mom. 

The two talk, Becky tells the customer exactly what Sam had told her, the customer is miffed, Sam gives her her receipt and moves on with his life. Good times. 

There’s a lull in business, and Sam takes the opportunity to ask Becky if he can go ahead and take his lunch, considering there was going to be a rush in about an hour, when his lunch was actually scheduled. Because, you know, scheduling. 

He switches off his register light and makes his way to the service desk, but he runs into Becky before he gets there. She’s standing next to Zachariah in the middle of the store, writing something on a clipboard, and wearing a strangely serious expression. Sam starts to feel some regrets, because talking with the store manager is on par with carefully pulling your own teeth; both take lots of effort and concentration, both cause a ridiculous amount of pain, and both are completely stupid and useless activities, unless you’re Tom Hanks stranded on a desert island with a toothache. Um, that analogy went a little off topic. Anyway.

Sam steels himself and walks up to the pair, putting on a smile and saying, “Hey, can I talk to you for just a sec, Becky?” 

They both look up, and Becky smiles. Zachariah smiles too, but his smile is a lot scarier and less like he’s in love with you, so Sam focuses on Becky. “Of course, Sam!” Becky quickly lowers the clipboard and turns her full attention to Sam. “What do you need?” 

Sam shoots a small glance at Zachariah before responding, “I was thinking I could take my lunch now, before the 5:00 rush. That okay with you?” 

Becky is obviously about to say yes before Zachariah, the dickwad he is, butts in. “Are you scheduled to have your break time now? This is probably not what you want to hear, but we need to make sure all the breaks follow according to schedule. I need to treat everyone equally; work smarter, not harder. We’re in the middle of a paradigm shift. You need to square the circle, and we need to be able to manage their expectations while focusing on value! It is what it is.” 

Wait, what? No seriously, what on earth did Zachariah just say? It’s like he googled ‘things that bosses say’ and just spewed out the first 8 responses. Fucking bosses. 

Sam decides to grin and bear it. Or at least, roll his eyes subtly and bear it. Maybe not so subtly. 

As he walks back to his desolate register, Sam lets his mind wander to the receipt that’s been metaphorically burning a hole in his pocket, the one with Gabe’s name and number on it. The one he’s almost called a couple times in the past week or so since he got it. Gabe honestly seemed like he was totally Sam’s type, from the little they had spoken, but you know, Sam kinda sucks at the whole dating thing. Hell, he didn’t even know if the number was an invitation to date; it might just be a cute guy fishing for a new number for booty calls. (Ew, Sam takes a moment to hate himself for thinking the word “booty.” Shit, he did it again.) With the amount of terrible flirting he had done with the guy, maybe Sam had given him the impression he was actually into one night stands. Which he was not. At all. Sam likes love and commitment and maybe a few kinky ownership things. He doesn’t so much like hooking up with someone he doesn’t even know, just for the sake of pleasure or whatever. I mean, he likes sex! He just likes it to mean something. God, if he can’t even think without being awkward, how the hell is he supposed to actually flirt. This is why Sam will die alone. 

A few customers later, Sam sees a familiar face. Well, two faces, to be precise. He then decides it’s probably time to start a diary or something, because damn, life in retail was not supposed to be interesting. He’s supposed to be able to phase out and think about homework, not see the guy he’s interested in dating and the guy he’s been giving relationship advice to walking up to his register together. 

Oh dear lord, don’t let Gabe be the guy Cas is in love with. Please, Jesus W. Christ, if you exist, do this one thing. Please. 

“Uh, hey Cas,” Sam utters warily. “And… Gabe?” Just five hours till you can go home. Five hours till you can wash your hair and read Harry Potter for the thirtieth time. Come on, man.

Cas and Gabe both wore expressions of surprise at Sam’s words, and they quickly turn to each other. 

“Gabriel, I was not aware you were acquainted with Sam,” Cas stutters.

“I could say the same to you, bro.” Gabe chortles, “Small world? Or, small town, I guess. Small number of grocery stores nearby.”

‘Bro.’ Is that a ‘I’m trying to make you think I’m not into you and we’re just friends,’ bro? Maybe they’re actual brothers? With names like ‘Castiel and Gabriel,’ Sam doesn’t find it too hard to believe. And in no way shape or form had Gabe come across to him as the raging hetero that Cas had previously described to him.

Cas clears all the confusion up with one sentence. “Sam, this is older brother, Gabe. I believe I have mentioned him in passing?” Good. Thank you, Jesus. I swear I won’t watch porn for the rest of the week. Or at least, the rest of the day. 

Sam throws on a semi-real, very confused grin and says, “Yeah, you did. Uh, and Gabe, you mentioned a younger brother, so I guess that’s you, Cas.” Huh. Small number of grocery stores nearby, indeed. 

“Well this is fun!” Gabe titters, looking from Sam to Cas and back to Sam. “So how to you two know each other? School, I’m guessing? I feel like I would’ve remembered you talking about our studmuffin here though, Cassie. Not that you would have properly described him, but still. You two aren’t dating or anything, are you? I was kinda hoping for a piece of that myself, but I’m not cockblocker, so just say the word, and I’m out.”

The apparently only two members of the conversation with the ability to be embarrassed both  
blush a tad and generally look awkward. Gabe… gloats? Is he gloating? Yeah, he’s totally  
gloating. Sam decides yet again that it’s time to move to Canada. Why hasn’t he done that yet? 

“Actually, we met in the same was as you and I did, Gabe. Cas came into the store a few weeks ago, and we kind of hit it off.” He adds with no small amount of haste, “And we’re just friends.”

Gabe was more and more seeming like a bit too much of a dick for Sam’s taste, but at least he wasn’t great at social situations. That’s always a plus. 

“Well I say again, small world.” Gabe grins again. Sam wonders how much plane tickets to Alberta would cost and if it’d be too hard to transfer to a school in some city like Edmonton. He’d always heard nice things about Edmonton. 

During almost the entirety of the conversation thus far, Cas had been staring sullenly at his shopping basket, and he finally starts placing their items onto the conveyor belt and Sam watches inconspicuously. Bag of candy, cheap toilet paper, milk, eggs, bag of candy, brown sugar, green onions, bag of candy, Old Spice deodorant, six pack of beer, baby carrots, peanut butter, nutella. 

Sam lets the awkwardness take him, body and soul. He embraces his own uncomfortableness and lets it feed his very soul. He is stronger than this. He can make smalltalk. He is the master commander. 

“So, Cas, how are things going with your relationship problems?” Nononononono, bad Sam! That is not smalltalk. That is big talk, and the guy you have a stupid crush on is right here, and it’s the other guy’s brother, and this is stupid and bad!

Cas drops the jar of peanut butter loudly onto the conveyor and looks at Sam with wide eyes, then turns to look at Gabe. Shit, Gabe doesn’t know. Not only was this not smalltalk, Sam just spilled one of Cas’ secrets in front of the guy’s brother. Why are social situations so hard??

Gabe turns his somewhat predator grin upon his brother, and Sam wonders if he’ll get fired for running away right now. Like, straight-up running away. “Why Castiel, I didn’t know you were having relationship problems! Why didn’t you tell me? You know how great I am at relationships. I’m a veritable love guru.”

“No, you’re not,” Cas grumbles, regaining his composure and righting the peanut butter. “And I’m not having relationship problems. Sam is merely referring to the troubles I am experiencing through and because of my familial relationship with you, Gabriel.”  
“Ouch,” Gabe replies, appearing rather stunned. Apparently Cas doesn’t say mean things very frequently. Not that that should really qualify as mean; Cas was really more like an angry puppy than anything else. 

The rest of the transaction is unbearable uncomfortable, the painful silence interrupted only by a quick, “Your total is $37.85,” from Sam. Finally, they say their goodbyes, and Sam sighs as he watches the brothers exit the store. 

Right before stepping out the sliding doors, Gabe turns around, lifts his hand to his face like it’s a phone, and mouths the words, “Call me!” 

Yeah, like that’s going to happen. Sam pinches the bridge of his nose and wonders if he was dropped as a baby or something. How else could he actually be this awkward?

**Notes for the Chapter:**

> Please let me know what you think! Was it stupid? A bit, yeah. But was it funny? Well, that's up to you to decide! (Please comment. It gives the tired writer within me a reason to keep writing)


	4. Tortuous Texting

**Notes for the Chapter:**

> I'm so sorry this is a week late! It was kinda hard to write, and also, I've been pretty busy lately. ~~Also~~ I might have not proofread this chapter either... Sorry! *ashamed author sounds*

It’s an enigma to the population of people who do not work in retail that grocery store employees buy groceries too. Someone in their uniform but without their name tag walking, around the store with a shopping cart full of food? They’re definitely on-duty, ready to serve. So they have half a granola bar stuffed in their mouth? Well, that’s the best time to ask them a question! Sam can’t wait to get a proper job. 

He swallows the bite of his Luna bar (he can be a strong independent woman if he wants, so shut up), and smiles at the customer who just asked him where the cleaning supplies are. “Those are gonna be around aisle 38, ma’am.” Ever the conscientious employee, Sam always answers all questions posed him, even if his impulse buy ice cream is melting in his cart as he speaks.

The customer smiles and heads off to the aisle, and Sam continues on his merry way. 

He stuffs the other half of the Luna bar in his mouth. 

“Um, sorry do you work here?” A disembodied voice queries.

Sam rolls his eyes, turns around, swallows the Luna bar, and smiles at the squwat man with a basket in hand, looking up at him. 

“Yes I do; how can I help you?” Sam had just gotten off of a 9 hour shift, and as ready as he was to go home, he really didn’t have any food back at his apartment, and buying stuff from the grocery store was way cheaper than going out for fast food. And healthier. Though, he is buying ice cream… but it’s a one time thing. For sure. Definitely. 

“Can you let me know, do you y’all sell fresh cut flank steaks in your meat area? I didn’t want to walk all the way over there if you didn’t even have what I wanted to buy, though it really seems like you ought to.” Sam has a love/hate thing with people who say “y’all.” On the one hand, they have a tendency to give you free food and be nice to straight, white people. On the other hand, they’re usually dicks to everyone else. Sam doesn’t want to generalize, though.

Sam smiles and replies, “You know, I don’t actually work in that department, so I couldn’t tell you off the top of my head, but I can point you at someone who does.” He has no fucking idea, and he’s not supposed to be working, so. 

The man sighs and mumbles something under his breath about how at the other grocery store, everyone knows where everything is, and maybe he should just go there. Sam doesn’t care. Does he thinks Sam cares? Sam does not care. 

Sam points him toward Becky, who’s standing nearby, glancing at a notebook. and frowning.

Finally, Sam can get on with his shopping. 

It had been a normal day of work; nothing extraordinary happened other than Careless Whisper playing over the storewide music system. He’d been thinking a lot about texting Gabe, actually. It’s not that he’s lonely, per se. Just. Um. No, fuck it, he’s lonely. It’s just about a month until school starts back up, but most of his friends went on cross cultural trips this summer, and been he’s dying in a pool self pity and feelings of abandonment. So yeah, despite his better judgement, he wants to text Gabe. It’s been a little over a week since the awkwardness of seeing him and Cas together, and Sam feels like he doesn’t really have much of anything to lose at this point. 

So he pulls out his phone. 

And then puts it back in his pocket after thinking for 0.2 seconds and hurries down a random aisle, because no. He is not this desperate for love. 

Nah, he totally is. He pulls his phone back out and selects contacts (because yes, he put Gabe’s number in almost immediately after getting it, because ya know, loneliness). He thinks for a while about wording, then decides on an okay text and hits send.   
Sam: 

He feels almost instant regret and shoves his phone once again into his pocket. Desperation pushes people to do crazy things… 

A few seconds later, Sam feels a buzz and figures it’s Gabe texting him back. Eager much? Eh, who’s he to judge? He pulls out his phone and is taken off guard when he sees a text from his brother, Dean. 

Dean: _Hey bro, long time no talk. I’m in your neighborhood, wanna hang?_

Huh. Okay. Weird. Sam seriously hasn’t heard from his brother in ages. Something is probably wrong. Ugh, maybe dad had a heart attack or something. Shit, he might just have, actually. Or maybe Dean is in some kind of trouble. Or maybe he has cancer, the doctor gave him three months left to live, and Sam has wasted the past few years that he could have spent with his brother. Sam’s brain rolls over a few other worst-case scenarios before pulling himself out of that deep dark hole and thinking happy thoughts. Like dogs. How lucky are humans to have dogs? Super lucky. They’re sweet and selfless and the perfect companion in all situations. Sam should get a dog. All right, back on topic. No freaking out. Dean wants to meet up. Cool, right? Yes, cool. It’ll be good to see him again. 

Just as Sam is seriously considering what the hell he’s going to write back to Dean, his phone buzzes again. He glances at it, and this time it is Gabe. 

Gabriel (the cute guy from work): _Sure am, Sam-o! You free tonight? Something tells me we can have lots of fun together ;) Hmu~_

Oh fuck, Sam had kind of forgotten what Gabe was actually like. But, he needs this. At least, he thinks he needs this? He probably just needs a dog, but that’s too expensive for his current state of life. And too much responsibility. Ugh, Sam just wants a dog, though. 

He oscillates for a couple minutes between thoughts of the two people he now needs to text back, and he’s starting to feel an aneurysm coming on when he catches the eye of a familiar face across the aisle from him. 

It’s Castiel. Sam is fairly certain his brain explodes at this point, though only psychologically; physically, he loses a few years of life and gains three grey hairs. 

It’s not that he doesn’t want to see Cas; on the contrary, the guy is awesome, and Sam could really use more friends (as previously stated). But Sam is tired. Sam is confused about why his estranged brother is texting him, wanting to meet up. Sam is conflicted about whether or not he wants to get involved with a guy who might be slightly crazy. Sam’s ice cream is probably completely melted by the point. Sam wants to go home. Sam doesn’t feel like he has any relationship advice to give at all, especially not to the sibling of the man who he is interested in and the guy he accidentally offended the last time he saw them. Sam is tired. 

Sam manages to slap on a smile, “Hey Cas!”

Castiel smiles too. That’s good. Unless it’s fake and Cas has decided he is going to murder Sam for their last conversation. Sam should probably pick up meditating or yoga or something.

“Hello Sam; it’s good to see you.” Cas walks up, patent trench coat flapping half-heartedly behind them. 

“You too, man.” Sam pauses for a second, then adds, “Look, about last time, I’m really sorry I--”

“No, no, I should apologize,” Cas interrupts. “My brother had been bothering me all day before we saw you, and that simply was the last straw for me. I lost my temper, and I’m sorry.” 

“Oh no, it’s cool. I’m really sorry I didn’t think before bringing up the boyfriend thing. I guess I’m just a little awkward around Gabe.” And around everyone else, too. Basically, a fucking socially inept moose.

Cas tilted their head a little, “Why are you awkward around Gabe? In fact, how do you two know each other? I recall you said you met in the same way as we did? But he didn’t give me any specifics. In fact, he was rather quiet this whole past week, which is unusual for him… but I digress.”

“Uh, yeah, he came through my line here one day, and I guess we kinda hit it off?” Sam isn’t too sure how much he wants to tell Cas about, well, anything Gabe-related. It’s confusing. Ah, but who else knows Gabe well enough to let Sam know whether or not he should actually date him than Cas? “Well, I guess it wasn’t so much hitting it off as hitting on each other… But I don’t know. Like, he seems really nice, but he also comes on a little strong, you know?”

“Yes, I definitely know what you mean, Sam.” Cas nodded sullenly, then added, “He hasn’t had a relationship that lasted longer than two months for that very reason.” Suddenly, Cas looked embarrassed and started fiddling with the edges of his coat. “I guess I really shouldn’t have told you that. Sorry. I mean, he’s a wonderful person! He just has trouble with being, um, serious. About anything.”

Sam smiles a bit and nods. He gets that. Well, not specifically about not being able to be serious, but it sounds like basically any of the crap Sam does to deal with life. Some people laugh at everything, some people work through everything, some people sleep through everything. Nobody is perfect. 

Before Sam could respond, Cas continues, “Have you seen Friends? Like, the show.” Sam nods. It’s a fucking classic. “Well, he’s kind of like Chandler.”

Sam grins, “Well, I’m a bit of a Monica myself, so maybe it’ll work after all. Wait, you’re Phoebe, right?” Sam prides himself on being able to match everyone he’s ever met with the correct Hogwarts house and which Friends character they’re most similar to; it’s his greatest skill. 

Cas also grins for a second, “Yes, as a matter of fact.”

So, does that make the not-a-boyfriend Joey? Or Paul Rudd’s character?/ Fuck, what was his name? Mark? No… It wasn’t David. Okay, Sam, back on topic. You’re alienating the people reading your mind right now who haven’t watched Friends. 

“Well, I’m guessing you think I should give him a chance?” Sam honestly can’t shake the feeling that Gabe is more than just an obnoxious jokester with a sweet tooth, and he doesn’t think he’d be able to keep himself from going out with him, even if Cas advised against it.

Fortunately, Cas responds with a carefully polite affirmative, and Sam lets himself feel relieved. 

“So, what about you? Any progress with Mr. “Straight” Best Friend?” Yes, Sam used finger air quotes. No, he’s not ashamed. Not at all. 

Cas smiles and shrugs. “I suppose in a sense.” They stop. Sam waits. Cas doesn’t continue. Huh.

“And…?” Sam prods.

“Well, I’ve discovered he is bi.” Cas doesn’t look excited enough. Why isn’t he excited? That is great news, right?

“Okay, and? You don’t seem overly thrilled.”  
Cas shrugs again. “Well, I guess I just feel a little discouraged. I mean, he’s interested in men, and he hasn’t shown any interest in me. I kind of liked it better when there was a reason for him not liking me in that way. Now, I can only assume it’s me; there’s something about me he doesn’t like.”

And Cas is pulling out the sad puppy face again. Oh heavens. How could a grown adult look so pathetically adorable?? Nuh uh, no way was he letting this continue. 

“Dude, no. First of all, I still think he might like you. Second, he doesn’t deserve you if he doesn’t see how amazing you are. Third, it’s his own fault if he doesn’t like you like that, because you are very attractive and nice and great, so yeah, screw him. Um, fourth? Am I on fourth? Yeah, well, um, screw him again. You seriously are awesome, and you don’t need him.” Sam nods to himself as he finishes and crosses his arms authoritatively. 

Cas smiles, “Thank you, Sam. And, as you said, I don’t technically know how he feels about me; I just know he hasn’t made a move thus far.”

“But neither have you!” Sam interjects enthusiastically. 

“Yes, you’re right there,” Cas hums, then seems to notice the time. “Oh my goodness, I really need to get going; I’m supposed to be meeting him for dinner tonight, and I had no idea how late it was. 

Sam waves him off, then glances down into his cart. The fucking ice cream is dead at this point, he’s 99.9% sure. Would it be too dickish of him to put it back and get another one from the freezer? Eh, screw it, he’s wants good ice cream. He fucking deserves good ice cream. Before making his way back to the frozen section, he remembers that he still needs to text Dean back, and he writes out and sends a reply.

Sam: _Hey man, I’d love to catch up. Hmu with when/where? Talk to you soon._

He’s standing in the middle of the ice cream aisle when he remembers Gabe. Fuck, so many texts to send. He’s not used to this. Huh, maybe he doesn’t mind being lonely so much after all… He types up his quickest, least witty text ever (yes, the dreaded, “Ok, when?”), then crams the melted mess into the back of one of the freezers, and grabs a fresh pint, before uncomfortably walking away and praying to Talos that nobody witnessed that. Not that it’s illegal or anything; it’s just looked down upon. By everyone. Including himself. Whatever.

**Notes for the Chapter:**

> Let me know what you think? I'm having so much fun writing this, and I can't believe I'm at 800 hits; thank you guys soooooo much! See you all next Tuesday!


	5. Broken Brother

**Notes for the Chapter:**

> Holy hand grenade! I'm so sorry this is late again! Maybe I was being too ambitious when I said I'd update once a week...well, this chapter is a little longer than normal and more angsty than ever before, so I hope that makes up for it? 
> 
> Oh, and I swear that one of these days I'm going to start editing my chapters BEFORE posting them. Just, not today. So sorry about the, uh, shit.

Socks. Fucking socks. Sam is a pretty cleanly guy; everything in his small apartment has its place, and he likes it like that. But Sam’s damn sock drawer is empty. How?? He literally did laundry two days ago, and he has plenty of clean clothes! Why is his sock drawer empty? Why, god? He spots a dime in the back corner of the drawer and picks it up. Fucking socks. 

He glances around his empty apartment for any socks that might have slipped his eye, grimaces, and decides to tough it out and wear the pair he had worn all day yesterday. He’s a big boy; he can do this. Athletes foot be damned. 

Last night had been great, though, and even the sock deficit couldn’t ruin his residual good mood. His first date with Gabe had been last night, and it honestly went way better than he could have hoped. Gabe had been almost nervous? Well, maybe not nervous, but he’d been gentlemanly and somewhat subdued, at the very least. He had acted much more like when Sam had first met him, and Sam chooses to see that as a good sign. 

The night itself had actually been rather bland, surprisingly enough. They had gone to a bar, had a couple drinks, and talked. The conversation covered Sam’s major, Gabe’s childhood, Sam’s love of dogs, Gabe’s pursuit of an MA, and lots of less serious things, like the idea of kale ice cream (it was decided to be a terrible idea) and tea vs. coffee (they both tended towards liking coffee better, but they agreed that tea drinkers were probably the coolest people alive). The night had ended the two of them agreeing to go out again soon, only for dinner next time. 

And just like that, Sam had been ruined for other men. He runs a hand through his hair, then actually, physically slaps himself. It hurts, and he’s a little embarrassed. BUT, not as embarrassed as he is for having fallen head over heels for a guy he basically just met. (He actually spends a few minutes considering the logistics of a 6’4 man like himself being flipped head over heels, realizes his brain is doing that stupid thing where it devotes his precious little daily mental capacity to thinking about something moronic, and slaps himself again.) 

Love does crazy things. Well, not that this is love. No, it’s probably just a crush. A stupid crush. Sam needs more hobbies. 

Speaking of devoting mental capacity to things, Sam needs to figure out whether he should drive to his lunch date or just walk. After some texting, he had made plans to meet Dean for lunch today to catch up, and the meeting place they had agreed on wasn’t too far from his apartment. He’ll probably just walk and save on gas money. He looks at his watch, sees that he has about fifteen minutes before the time he and Dean had set to meet, grabs his wallet, phone, and keys, and heads out. 

It’s a cool day for early August, and the walk is actually really nice. A brisk ten minutes of walking later, and Sam is five minutes early at the nostalgic diner he told Dean to meet him at. It’s nostalgic, because growing up, their dad had to move around almost constantly for work, and the boys had to do all that traveling with him. Sam’s childhood had been packed with sleazy diners, cheap motels, being a constant new kid at school, and gradual learning to hate his father. Well, hate is a strong word. Disrespect though? Yeah, disrespect fit the bill. I mean, what kind of asshole dad puts himself before his two sons? Granted, he hadn’t just dropped them somewhere to live on their own, and Sam is pretty sure he probably did all that work because he thought it was best for them. But still. Dick move. 

Sam lumbers into the diner and scans the cozy room until he spots a familiar face. He can’t help the grin that slides onto his face at the sight of his brother, and he crosses the room in four long steps before pulling Dean into a tight hug. He steps back after the embrace and grins again. 

“Heya, Sammy.” Dean’s shorter than Sam remembers. Huh.

“Good to see you, Dean.” They both stand for a minute like that, smiling at each other and having a ridiculous chick flick moment, before the awkwardness starts to develop. Oh yes, wherever Sam goes, awkwardness is sure to follow. Always. 

They sit down at a booth and an uncomfortable silence falls while Sam tries to think of something to say. He finally settles on, “How’s it going?” Dear lord, this is already going swimmingly. 

Dean snorts. “I’m doing okay, Sammy.”

Sam nods and chews on his lower lip. Finally, a waitress comes up to interrupt the actual torture they had been experiencing and asks if she can get them anything. Sam asks for an unsweetened tea and a house salad; Dean gets a root beer, a triple bacon cheeseburger, and a piece of blueberry pie. Okay, so he hasn’t changed too much. 

As soon as the waitress leaves, Sam decides to not let any more awkward silence happen today. “Soooo… what’s been going on with you for the past few years?” It’s a start. 

Dean smiles and cracks one of his knuckles. “Not a lot. Dad’s doing all right. Misses you like   
hell. Old bastard didn’t realize how big a part of his life was yelling at you until you left.” They   
both huff laughs, but it’s kind of melancholy. “I’ve been working at Uncle Bobby’s garage, which is why I’m in town.” Dean pauses for a second and seems to mull something over before going on. “Well, okay, actually he sold it to me, and I’ve been living around here for a while. Sorry I didn’t tell you about me living here until now; I guess I was a little nervous about it. But yeah, Bobby decided he wanted to retire. Dad’s still working, but he spends half his time with Bobby anyways. They both act like a couple of old farts, even though they’re only in their 50s. It’s nice though; I think they’re both pretty happy. Running the garage is nice, too.” 

Oh. Huh, okay, cool. 

Wait, what? Dean’s been living in town, and he’s only just now telling Sam? What the fuck is up with that? What was he nervous about? He literally has nothing to be nervous about; Sam is not someone who makes people nervous. But that’s actually really nice. Sam and Dean has a sort of adoptive uncle who’s been a friend of their dad’s since prehistoric times, and he owns, well owned a garage on the outskirts of the college town. It’ll be great to be able to see Dean more frequently now that he’s probably living within half an hour of Sam. 

Still, something seems a little weird, like something is off with Dean. He decides he might as well press it. “So, uh, why were you nervous about telling me you lived nearby?” 

“Well, no reason really. I guess just because we didn’t really part on great terms when you left. And dad and I aren’t really in a good spot, either. I guess I was just worried I might, I don’t know, say something stupid.”

“What do you mean about you and dad? Did something happen?” 

“I mean, it wasn’t anything big.” Wow, Dean is starting to look ridiculously shifty. Like, not in a creepy murderer being interrogated kind of way, but in a scared witness kind of way, you know? “I, uh, well I guess I said some stuff to him that he didn’t really like. But the guy’s an asshole, so I don’t really care what he thinks. But I guess it’s kind of made me a little, um. Well, you know what, it’s really not important.” 

Shit, what the fuck? Dean literally used to tell Sam everything when they were little. Sam had actually been the only person Dean would open up to, and there were never any secrets between them. At least, on Dean’s side. Sam had kind of been a sneaky bitch as a kid, but he’s a Slytherin, so that’s normal. Uh, off topic. Anyway, Sam is getting a bit worried, but he decides not to push Dean for anything, because this is just a catching up lunch date. Sam does not need all the details of Dean’s life. Sigh.

“Hey, you don’t have to tell me anything you don’t want to, man.” I mean, it’d be nice if you did, because Sam is curious as fuck, but it’s whatever. 

Their food arrives. And all the people said Amen. But seriously, Sam is getting weird vibes from Dean, and he honestly doesn’t know what to think of it. It’s like Dean has some kind of secret he’s keeping or something, but Sam has no idea what it could possibly be. What does Dean have to hide from Sam? 

They sit and eat. It’s pretty uncomfortable. 

And then the proverbial dam breaks. 

Dean sets his half eaten burger down, looks up at Sam, sighs, steels himself, says, “I think I might be gay,” then picks his burger back up and rips a voracious bite from it. Ohhhh… Yeah, this makes more sense now. 

Sam grins, then laughs at Dean’s startled response to seeing Sam’s happy reaction. Oh yeah, this information would definitely create a rift between anyone and John Winchester. Everything is making a bit more sense now, to be completely honest. 

“That’s great, Dean!” Sam thinks for a second, then adds, “But wait, like actually gay? Because I’ve seen you with a lot of girls?”

Dean scowls and fiddles with the burger in his hands, which is totally disgusting to watch, and Sam tries not to look down at his brother’s hands. “Look, I don’t know anything about this. I guess I’m whatever it is when you like both. Or either. Whatever. But yeah, dad wasn’t happy when he found out. I mean, he didn’t fucking disown me or anything, but he definitely thinks I’m a gross human being now. Which is fine; I don’t give a shit what he thinks about me. I’m just a little, uh, lost? Jesus, I haven’t talked to anyone about this except my best friend, and it’s actually super fucking embarrassing, so can we maybe move on?”

Sam’s permanent grin doesn’t falter for a second. “‘Best friend?’ Or boyfriend...?”

“Shut up, bitch.”

“Jerk.” Oh my god, so many chick flick moments today. If Sam didn’t unabashedly love chick flicks, he’d probably be getting a little nauseated by now. 

Something is still bugging him though. It’s probably nothing, but Sam needs to ask to make sure.   
“Hey, um, you’ve known about my sexuality for as long as I have, so why were you nervous to tell me about it? Or… was there another reason you were worried about talking to me?” 

Dean’s smile stutters, and Sam knows there’s something else. “No man, that was it.” 

“Dean, you’re not actually a good liar; you know that, right?” 

There’s some extended silence while Dean thinks about, uh, something. Sam isn’t a mind reader, but it’s obvious his brother is working something around his mind. 

Finally, he murmurs quietly, “I guess I’m sorry.” 

“Sorry? For what?”

“I… I’m sorry I didn’t talk to you for so long. I’m sorry you had to leave. I’m sorry dad was such an asshole to you.” The more he talks, the more his words accelerate. His self control looks like it’s slipping, and Sam feels an ache deep in his heart. “I’m sorry I didn’t take better care of you growing up. I’m sorry I didn’t tell dad where he could shove all his thoughts about who you were and what you did. I’m sorry I wasn’t there for you. I’m sorry you had to grow up so damn fast. I’m sorry I was such a bad older brother. I’m sorry I made you carry my problems instead of looking after you. I’m so damn sorry, Sam.” 

Oh shit. “Jesus, Dean, no. It’s okay. None of that stuff was your responsibility! You were a great brother, and none of the shit that dad did was your fault. Hell, nothing at all was your fault. And not talking in so long is on me, too.”

Dean shakes his head, and holy fuck, is he crying? Shit, he’s crying. Sam is so bad at serious situations, and oh my god, he’s going to cry too. Shiiiit. 

“Sammy, you were a kid, and dad talked so much shit on you. Mom wanted me to protect you, but I didn’t keep safe from him. I saw how much it affected you, and I didn’t help. It was the one damn thing I had to do, and I screwed it up. I was never going to be anything, but you. You were smart and brave and independant. My one job was to protect you so that you could be happy and okay, but I couldn’t fucking do it. You still managed, but damn it, you were miserable. You didn’t have anything holding you back there with us, and you had every reason to want to leave. I’m really glad you left us in the dust, Sam. You were always going to be better than dad and me. You and mom; you’re the best of us. Dad and me, we ain’t worth shit, but you, you’re going to be an amazing lawyer, and, and--” 

He cuts off. Sam doesn’t know what to say. He never knew Dean felt like this. He seriously had no idea. 

“Dean, you were the best older brother I could have asked for. You still are. And all that stuff about you being worthless? That is such fucking bullshit. You’re the best, kindest man I know. You’ve always done your best at everything you do; you’re loyal to a fault; you don’t compromise on your beliefs. In the least incestial way possible, you’re the Chandler to my Monica, which means you’re the best damn character in the whole show.”

Dean huffs. “Still making Friends references?”

“Yes, and don’t you fucking forget it.” They share a smile, then Dean rubs his face vigorously. Sam legit hasn’t seen him cry since middle school, and if this hadn’t been an actual serious discussion, he’d be very tempted to use it as blackmail material. 

“So, I guess that means you forgive me?” Dean is still looking nervous somehow, and Sam smiles sadly.

“There’s nothing to forgive, Dean.”

They talk for a little longer, not about anything actually important or serious. Sam gives a rough summary of his recent years at college; Dean describes his apartment and how quaint it is. Eventually, Sam brings up Gabe, which reminds him to ask about Dean’s newfound sexual preferences. 

“So, is there someone?” He really hopes there is, because oh my god, how cute will Dean be with a boyfriend? Ugh, he really needs to stop watching all those rom-coms. 

“Uh, sort of?” Dean scratches the back of his head and eats a bite of pie before continuing. “I mean, I like him--er, them. Sorry, they’re nonbinary. I’m really trying to get used to all this, but it’s fucking hard when they look like a guy but aren’t. Anyway, they’re my best friend--”

“Ha! I was right!” Sam’s triumphant interruption is met with stony silence

“As I was saying, they’re my best friend, but I don’t know if they’re into me. We were actually talking about sexuality and stuff, and I told them I was into guys, but they didn’t try and make a move or anything. Honestly, they’re way too good for me, which is why I haven’t asked them out or anything. Like, I’m happy being roommates and best friends with them, if I’m being honest.”

Huh, sounds like Cas’ situation, but like the reverse of it. Wait, there’s no way… “Uh, if you don’t mind my asking, what’s their name?”

Dean grins, “It’s actually really weird. I think their parents were super religious or something, because they’re named Castiel. I just call them Cas, though. It’s funny, apparently nobody had ever given them that nickname before me. Uh, Sam? You all right, man? You’re kinda phasing out on me, man.” 

What. The Fuck. No seriously, what the fuck?? 

“Uh, yeah, sorry. I just actually know Cas.” What the actual fuck. Sam.exe has stopped working. 

“Oh really? Ha! Small world! Or, small town, I guess.” 

Shit, no, that reminds him. He’s dating his brother’s boyfriend’s brother. Nonononono, this is too fucking weird. 

They talk for another thirty minutes or so before Dean says he needs to get going and Sam agrees that they should definitely meet up to talk again soon. Walking home, Sam’s brain is doing fucking cartwheels, because holy fuck, this is the weirdest shit that’s ever happened to him. 

Suddenly, he has an epiphany. He’s seen BBC’s version of Emma enough times to know that he can’t let this perfect matchmaking opportunity go to waste. There is a future of love and happiness at stake, and he is up for the challenge. He’s going to make Cas and Dean admit their latent feelings of affection for each other! Fuck yes. He’s got this.

**Notes for the Chapter:**

> Let me know what you think?? (Pls? I can't write without comments...because I suck at writing.....) Anyways, thanks again for all the support! It's seriously so awesome that people are reading this! ^-^ 
> 
> Also, thoughts on the angst? Did I do okay keeping it close to the characters? I'm deadass nervous you guys are going to hate this, because I've never actually written anything non-comedic before...


	6. A Moose and His Mouse

**Notes for the Chapter:**

> Sooooo sorry this is late! ...again... Look, it's senior year, and I'm dying; cut me some slack *cries a million student tears*
> 
> By the way, I just posted a Destiel mailman AU oneshot! If you like this story, you'll probably like it too, and I'd love it if you read it and maybe gave some feedback?

Sam: _Okay, so you’ll be here at about 5:30?_

Gabe: _sure thing, sweet cheeks_

Gabe: _oh and I’ll be in a purple vw bug… not easy to miss_

Sam: _Why am I not surprised?_

Gabe: _what can i say? I love my car_

Sam: _See you soon =)_

Tonight is Sam and Gabe’s first proper date. Unfortunately, school has begun, so neither of them actually have any free time for dates. Thus, Gabe is picking Sam up straight from his 9-5:30 shift at the grocery store, and they should have almost three hours together before Gabe has his ridiculously late psychology class. Seriously, whose idea was a fucking 9pm class? 

Sam isn’t hyped to be in his work uniform during their first proper date, but it was either this or they could wait another week for their schedules to align again. As much as he felt silly for even thinking about it, Sam is really loving spending time with Gabe. Well, texting is basically all they’ve done for the past week or so. Going out for drinks was awesome, and just chatting with Gabe is really fun. It turns out they actually has several things in common, like they both are huge fucking geeks, and they both went through awful goth phases that they’d rather forget about. 

Sam feels like his life has become as chick flick, and he honestly can’t find it in himself to care. With the whole Gabe thing, plus the huge fucking Dean and Cas thing, this summer had basically turned his life upside down. Which is cool. Sort of. 

Okay, Sam is damn tired. He never thought he’d miss his boring life, but Jesus W. Christ, it’s like a fucking soap opera up in here. 

Anyway, Sam is still on the clock. Granted, it’s the least busy Wednesday night he’s ever worked, but he should probably be doing _something_ work-related. Like sweeping? He’s got another 15 minutes before he gets off, so sure, he could do sweeping. 

A completely uneventful 15 minutes later, Sam is clocking out, pulling off his work shirt to reveal the plain black t-shirt he wears underneath it, checking his hair in the glass of the cigarette case, and making his way out to the parking lot to look for Gabe. He shoots him a quick “hey, I just got off,” but he spots the infamous purple VW before Gabe can respond to the text. And damn is it purple. Oh and, holy shit, Gabe has those disgusting fake eyelashes attached his headlights. Sam valiantly tries to not throw up in his mouth, because ew. Ewww… This is the car of the guy he’s dating! Ewwwww… 

A hop, skip, and a jump and Sam in knocking at the passenger’s side window for Gabe to unlock the door. Gabe grins all too mischievously as Sam crams his huge body into the tiny fucking car, and Sam glares a bitch face at him. 

“No offence, but I want to tear the eyelashes off the front of your car and melt them into nonexistence.” 

Gabe grabs his chest and screws up his eyes. “You’re so mean!”

After a terse moment, they share a laugh, but Sam still wants to destroy the eyelashes. He has murderous passion against them. 

“So, where we going?” Sam inquires. They hadn’t really talked about what food either of them wanted, but Gabe seems to be driving with purpose, like he already has somewhere in mind. 

Gabe cackles secretively. “You’ll have to wait and see Sammoose; it’s a surprise.”

Did he just call Sam ‘Sammoose’? “Did you just call me ‘Sammoose’?” 

“Sure did! You’re tall and majestic like a moose! Also, I’m pretty sure if a moose were a person, they’d wear flannels all the time and have long, luscious hair like yours.”  
“But, you still called me a moose… I feel like I should be insulted.” Granted, Sam knows next to nothing about the mammal, but somehow being called one just feels rude. 

Gabe rolls his eyes. “Baby boy, you forget that I know a lot about animals. Allow me to properly inform you of exactly how much like a moose you are.” Ugh, Sam had forgotten that Gabe had mentioned having a love/obsession for zoology. Awesome.

Gabe took the rest of the drive to the restaurant and made a verbal list of all the similarities Sam had to a moose, such as height (moose are the tallest mammals, Sam is the the tallest boyfriend Gabe has ever had), diet (moose are Algonquin, so is Sam for the most part), friends (moose are solitary creatures and have no friends; Sam begrudgingly admits that the same is mostly true for him as well), and the list goes on. 

“Okay, fine, but if I’m a moose, you’re a mouse,” Sam crosses his arms and pouts as they pull into a parking spot. 

Gabe just laughs, “Sure thing, sweet stuff.”

They climb out of the car, and Gabe grabs Sam’s hand (which does NOT make Sam’s heart skip a beat), and starts pulling him away from the nondescript parking lot. A few seconds later, and Sam can tell where they’re headed. 

“IHOP? Really, Gabe?” Sam asks incredulously.

“Everybody likes pancakes!” Gabe grins and just tugs Sam hand harder towards the restaurant.

Sam laughs. He should have guessed. “This is without doubt going to be the most romantic date I’ve ever experienced.”

“Don’t you doubt it,” Gabe winks, then releases Sam’s hand to hold open the door. 

They’re seated by an adorable old-ish hostess (who, by the looks she’s giving them, probably wrote gay fanfiction before it was cool as a teenager in the 1800s) at a small corner booth with a weird painting of an egg above it on the wall. 

A waiter comes up pretty quickly, and they both order and water but ask for more time to look over the menu before ordering their actual dinner. 

“I’m guessing you’re going to be getting the strawberry cheesecake pancakes?” Sam eyes Gabe as he asks, knowing the guy was very protective of his sweets and wouldn’t take kindly to Sam’s idea of trying one of the healthier menu options. 

“Actually, I was looking at that cupcake thing they’ve got going on,” Gabe replies without looking up. 

Sam has a pretty bad habit of trying to fix other people’s problems. And controlling other people’s lives… But jeez, if he know what’s best, then what’s the matter with sharing that information? And Gabe is at dangerous risk for all sorts of health problems, so. Yeah. 

“Um, hey, I could order for you if you wanted,” Sam tries to be inconspicuous, but Gabe’s eyes raise from the menu, and from the inquisitive look he’s getting, Sam knows Gabe isn’t buying that shit.

“I’ve seen what you eat, beanstalk. I’ll stick with my order, if you don’t mind.”

Shit. Sam doesn’t want to come across as a know-it-all, but sometimes you know, it’s hard. He just wants Gabe to be healthy… Wait, eurika! 

“Hey, what if I order for you, and you order for me? That way neither of us will order anything too outrageous, because the other one might make them eat something really awful.” Sam smiles proudly at his idea, because let’s be real, it’s not bad. He really hopes, Gabe with agree.

“Ugh, Saaaammmm…” Gabe rolls his eyes. “Why can’t we just order for ourselves and be content in our personal levels of healthiness…?”

“Because!” But wait, maybe Gabe is right. It’s literally only the second date. Huh, maybe Sam shouldn’t be so controlling on the second date. Or ever. Shit. Maybe Gabe hates him. Shiiiit. 

“Wait, Sam, before you start thinking you’re an awful person or something silly like that,” Gabe interrupts his silent reverie. “You’re right, let’s do it. Sounds fun, anyway!” 

Sometimes Sam wonders if Gabe is a mind reader After years of hiding his emotions, particularly from his father, Sam had never really had much experience with people knowing or caring how he felt, but that was spot on and kind of immediately put a stop to all the shitty thoughts he’d be having. Weird.

After probably two seconds, Gabe threw his menu down and laughed. “I know what you’re getting!”  
Sam rolls groans. “Your sudden enthusiasm scares me.” After some serious consideration, Sam decides upon a tasty looking omelette with plenty of meat and cheese so Gabe won’t complain too much. 

The waiter comes back around, and Gabe excitedly opens his mouth to order. “Yes, the Belgian chocolate pancakes, please!” 

“Wait, Gabe, those are literally the least healthy thing on the menu! It’s over half of a day’s calories and way too many carbs, man! I’m gonna have a heart attack if I eat that.” Sam doesn’t want to have a heart attack. Yet.

“I need to fatten you up, or you’ll be no good for cuddling,” Gabe retorts. 

“Fine then, you’ll be eating the, uh…” Sam looks back over the ‘healthy’ (translation: less than a fucking million calories per serving) section until he finds what he’s looking for. “You’ll be eating the egg white vegetable omelette!” He hands his menu to the waiter, smirking at Gabe’s scandalized expression. 

“You’re such an asshole!” Gabe scowls up at his grinning date.

“Don’t dish what you can’t take, _sweetcheeks._ ”

“Oh, don’t pretend you don’t love when I call you cute names,” Gabe pouts, not really selling the irritated vibe, instead looking more like a toddler who was told he couldn’t have a cookie. Which is sort of what he is. Huh.

Their food arrives, and they both grimace at their respective plates, equal disgust on their faces. 

“How much do we have to eat?” Sam asks warily. 

“Hey, this was your idea, fancy pants,” Gabe replies, glaring at his plate.

Sam shoves a hand through his hair, then grabs a fort and carefully cuts off a bite of the horrendous stack of pancakes in front of him. “First bite on three?” 

Gabe pitifully mirrors the action with a nod. “Okay; three, two… one!” 

They switch plates after that one bite and agree to never try and change the others’ eating habits again. 

“So how was lunch with your brother?” Gabe asks, a biteful of chocolatey diabetes in his mouth. 

“It was great, actually,” Sam responds with his mouth equally full, hoping to get a point across. Gabe starts chewing with his mouth closed, and Sam counts it as a success. 

“I’d almost forgotten what a great guy he is, to be completely honest. Oh, and turns out he’s living nearby now! Oh, and he told me something pretty funny, actually. ” Gabe nods amiably, encouraging Sam to continue. “Um, so, have you ever met Cas’ best friend? You know, the one he likes?”

“No… why do you ask?” Gabe eyes him suspiciously. 

“Well, get this: it’s Dean.” Gabe laughs a laugh of disbelief. “No no, seriously, I’m not kidding! I didn’t think it was true at first either, but it totally is! I mean, unless there’s another Castiel who lives in town, goes to the university, and has a huge crush on his seemingly-straight friend.”

Gabe sits in stunned silence for a second. “Wait, you’re serious? Oh my god, this is insane.”

“I know, right?! But like, we need to get them together. Please, I’ve been working on some plans to make them confess to each other, but I really need help on Cas’ side.” Sam hopes to high heavens that Gabe doesn’t think he’s creepy or crazy for wanting to get involved in their brothers’ love life, but he wasn’t kidding; he needs Gabe’s help for his plan. 

As a grins spreads across Gabe’s face, Sam realized he shouldn’t have been worried about whether or not he would be on board. “Are you kidding? Hell yes! Let’s make our brothers start having sweet, sweet romance.” 

“I have no idea why I thought you might not want to help,” Sam admits with a laugh.

“Me neither, Mr. Matchmaker.” 

They finish off their dinner while discussing plans, though they don’t really go in-depth, because they’re both too excited (and Gabe too high on sugar) to properly scheme.

They pay, splitting the bill because progression and stuff, then Gabe grabs Sam’s hand again as they walk out the door and back towards the car. Again, Sam is FINE. He is NOT freaking out about holding hands, because that would be silly. Totally. 

They talk quietly about nothing important on the drive home, Gabe still holding onto Sam’s hand, Sam’s heart still beating out of his chest.  
Gabe walks Sam up to the door of his apartment, and Sam really hopes that Gabe can’t read his mind, because wow, that would be so ridiculously embarrassing. Seriously, what if Gabe kisses him? Um, so what if Gabe kisses him?? It’s not like you haven’t kissed someone before, sissy. Hell, you should kiss him! But what if it’s too early? Or what if it’s too late, and he should have kissed him back at their first date? Shit, shut up, internal monologue. You’re not being helpful at all. But what it--

Gabe cuts off Sam thoughts for the second time that night, this time with a kiss. It’s sweet and soft, not heated at all. All the tension and stress in his body fade away, and Sam smiles into the kiss, feeling happy and at home.

**Notes for the Chapter:**

> Thoughts? I know this was a little different than normal, but I thought it was pretty cute~
> 
> Thanks again for all the wonderful people who have been commenting! You guys are the only reason I continue to write tbh...


	7. Hot Mess Chapter™

**Notes for the Chapter:**

> Hey guys! Sorry again for the big pause in between chapters. Finals have been a bitch, but I finally finished, and now I just have graduation! 
> 
> And also, I know this chapter is quite short, but my inspiration is like completely gone, sooooo. Yeah.

“Thanks; have a good one.” As the overweight middle-aged man waddles away from the register with his paper bag full of frozen peas, Sam sighs. Another day, another shift. It’s been about a week since his last date with Gabe, school has been pretty steady, work has been fine, he hasn’t talked with Cas or Dean in a while. Life is boring as fuck. Yes, texting and the occasional five minute visit with Gabe was a break from the monotony, but he had thought his life was about to turn into a soap opera just a few weeks ago! Where’d the drama go? The fun? The excitement? Ugh, it’s fine, though. He really does need to be focusing on school. Ugh. 

“Hey Sam, can you come over here for a minute?” Sam glances over his shoulder and sees Becky waving him over to the service desk, so he switches off his register light and jogs over.

“What’s up?” It’s 2:30 PM on a Wednesday, so the store is basically dead, and he honestly appreciates any alleviation of his boredom, even if it means talking to Becky. She’s honestly the closest thing to a creepy uncle he’s ever had. 

“Well, I was actually wondering something…” Oh dear lord, if she proposes to him, Sam will actually die. 

“Okay, shoot!” Shoot me. In the head. Please. Because you’re creepy and like me too much. 

“Well… You’re bisexual, right?” 

“Pansexual, yes.” Where is this going? Oh shit, she’d better not be about to suggest a threesome. 

“Well, I’ve noticed you hanging out with that one guy that comes in here pretty often--longish dirty blonde hair, always buying candy--and I was just kind of curious if you guys were together?” 

“Yeah, that’s Gabe, and we’ve been dating for a while.” Please, please, _please_ let that be the end of this conversation. 

But no. At the words, Becky perks up, and holy fuck Sam can only imagine the disgustingly graphic thoughts that are probably going through her head. She looks kind of like she’s about to start drooling, actually. 

“That’s so great, Sam! What’s he like? He’s pretty cute, and I know you probably have only the best taste, so I’m sure he’s a great guy too! We should go on a double date sometime!! I’m actually dating this friend of mine named Chuck. He’s not super hot, but he’s cute, and he’s a writer like me, though he’s actually published, I only really write for fun. But anyway, tell me all about Gabe! How did you guys meet? You’re really cute together!”

This is technically harassment, is it? Sigh. 

“Um, yeah, he’s really great. We met here when he came through my line back in June.” Sam carefully doesn’t acknowledge the double date offer, because an entire evening being forced to make non-work related small talk with _Becky?_ Kill him now. 

He makes an excuse about having to use the bathroom and escapes before Becky can ask about what the sex with Gabe is like. Not that they’ve had sex… 

Sam starts making his way to the bathroom on the opposite side of the store and lets his mind wander to Gabe. They’ve only been together for a very short amount of time. It’s completely normal to not have sex until you’ve been dating for longer! Very normal and okay. Yes. 

Okay, but what if Gabe wants to have sex and you’re going to scare him off with your stupid fear-induced celibacy? Because, Gabe’s a pretty physical guy, you know. And it’s not like they met in a fucking Bible study; he literally asked you out by implying he wanted to have sex with you--or at least, that’s probably what he meant by “having fun together.” What if Sam is going to ruin this whole damn thing?

Communication is the key to fulfilling relationships. Text him, you moron. 

Sam: _Hey, weird question, but bear with me: do you want to have sex with me?_

Nice. Short and to the point. Sam feels such immediate regret after sending it that he actually spends a few minutes researching ways to delete a text before it’s been read, but it’s no fucking use. Apparently there’s an app for it, and he almost downloads it, but then he sees that dreaded little “Read” thing, and well, that’s that. This is the end. He’s officially destroyed his love life for good. It’s over, kaput, finito. 

The little ellipse appears that tells Sam Gabe is writing a response, and he grits his teeth while he waits, until finally, the reply comes through.

Gabe: _what, right now? u alright hon?_

Sam: _Sorry, I don’t know what I was talking abt_

Gabe: _oh hell no ur not getting out of this that easily! tell me whats going on in that moose brain of urs_

Sam sighs. Communication is key. Just communicate, and he’ll understand.

Sam: _I guess I was just kind of worried you were mad because we hadn’t had sex or anything yet…_

Gabe: _wut the hell made u think that?! of course I want to bone that fine ass of yours but only when ur ready sweetcheeks_

Gabe: _we’ve both been stressed and busy and i don't mind waiting boo_

Sam: _Thanks for understanding, Gabe_

Seriously, holy fuck, Gabriel is an angel. That entire text conversation took place on the toilet, and as he walks back to the front end, he can’t help but laugh at how freaking stupid he had been for a minute. Thanks, low self esteem! (Thanks dad…) 

He only gets a few steps away from the bathroom when he hears a familiar voice. 

“Heya, Sammy!” 

Sam twirls around, very conscious of the beautiful floosh of his hair spinning with him, and grins at the sight of his brother, a six pack in one hand and pie in the other. Such a nice stereotype. 

“Hey man!” They do one of those bro hugs as a greeting before Sam gestures at Dean’s groceries and asks, “Stocking up?” 

“Eh, just on the essentials.” Dean smirks, then continues. “Hey, I know you’re busy with school and all that shit, but we should hang again sometime soon.”

Aha! This is it! The perfect opportunity! The time for the gears of Sam’s matchmaking plans to begin spinning! And Sam didn’t even need to bring it up, because Dean took care of that all by himself.

“That sounds amazing, man. You know, I’m actually free tomorrow night, if that would be good for you.” 

“Sure, I don’t have plans.” Sam feels like an evil mastermind, because Dean, poor, unsuspecting Dean has no idea what plans he has for tomorrow night. Well, first he has to call Gabe and make sure tomorrow night will _actually_ work. But it probably will! 

“Hey, do you mind if I actually introduce you to a couple friends of mine tomorrow night? I think you’ll like them both, and I know they’ll like you.” Nefarious Sam is the best Sam, he has decided. Maybe he watches Leverage reruns too much, but he’s pretty sure Danny Ocean couldn’t hold a candle to him right now. 

“That’d be fine, dude,” Dean smiles in response. 

They make plans to meet at a little diner near the campus at about 6:30, then Dean waddles off to buy his “essentials,” and Sam pulls his phone back out to call Gabe. 

The phone rings only once before he hears the telltale click of someone answering chased by a jovial, “Y’ello?”

“Hey, Gabe, it’s me,” Sam starts, then remembers that phone calls are the bane of his existence. Why didn’t he just text again? Oh yeah, because that’s not been working out so well for him lately either. Jesus, he needs to work on being a functional human being.

“Hey, Sammoose. Whatcha need?” 

“Can you get yourself and Cas to the Roadhouse tomorrow night at 6:30 to meet Dean and me?” The plan completely rests on having all four of them together at once. It’s simple, but effective, and is almost guaranteed to run smoothly! The perfect plan.

Gabe utters a quick, “Just a minute,” then Sam hears a muffled, “Hey Cas, you busy tomorrow night?” He waits patiently as a very difficult to actually understand conversation goes on on the other end, until finally, Gabe speaks back into the phone, “We’ll be there!” 

“Awesome” Sam inadvertently puts on a villainous grin as he continues, “Tomorrow night, we’re going to make them admit their latent homosexual feelings for each other!”

Gabe cheers, and they both have a laugh, because wow, they are such nerds. 

“I can’t wait, babe,” Gabe chuckles through the line. “But I’ve really gotta go; I technically shouldn’t have picked up the phone in the first place, except that I saw it was you calling.”

Sam’s heart does not melt at those words. Not at all. 

“Well, I guess I’ll see you tomorrow night, then,” Sam smiles warmly into the phone. 

“Yep, see you tomorrow,” Gabe responds, and _wow_ they’re not going to do that gross thing couples do where neither one of them will hang up, are they? 

No, they aren’t. Sam decides to hang up. “Okay, well, love you,” he utters, then hits the red end button and starts walking back to the front of the store. 

Wait a minute. Something about that was wrong. What was it…? 

Oh no. Oh god no. 

“Love you”?? What the fuck, Sam?! You can’t say that! What the actual fuck oh my god noooo Jesus W. Christ this is bad. Remember thinking you were going to scare him off by asking if he wanted to have sex? Well this is way damn worse, you idiot! Oh no, no, nononono… 

“Hey Sam, you all right? You look like you’ve seen a ghost!” SHut uP bECky. Sam has lost motor function. This is the end. 

“Yeah, I’m fine Becky. Just accidentally told Gabe I loved him.” Wait a minute brain, that is oversharing! Becky is not the right person to overshare to! This quite possibly the worst day of all time.

“Aww, that’s adorable, Sam! Did Gabe say it back?” disaster

Oh shit, he didn’t. Dear fucking god, let this day just have been a dream.

**Notes for the Chapter:**

> Thoughts? The end is slowly approaching!! Next chapter ~the PLAN~ will finally be revealed!
> 
> Can I just take a minute to say thank you to u/TheGuestReviewer? Because they're literally the only reason I'm still writing this fic... Seriously, comments are what fuel me, and they've commented on all the things *cries because what a blessing*


	8. Fuck Alliteration, Shit's Going Down (Part I)

**Notes for the Chapter:**

> What is up, my dudes? Y'all doing all right?
> 
> This chapter is dedicated to all you who've read this far. I never thought anyone would read this, and I've been overwhelmed by all the love and support I've gotten! We're getting closer to the end, and even though this isn't really a terribly long fic, it's my first, longest, and best, so I'll hate to see it go. OMG I SEE A DOG AND ITS SO CUTE 
> 
> Sorry, I saw a dog. Anyway, hope you enjoy this chapter!

Today’s the day! Sam got off work at 4:30, which had given him just enough time to come home, shower, pick out an outfit to wear tonight, and have a full half hour of free time to worry! Yeah, he hasn’t talked to Gabe since accidentally letting out the non-lesbian L-word yesterday. God, it would have been so much better if he’d just said “Lesbian you.” Not that that would have made sense… Okay, whatever. Anyway. 

He’s in a comfortable pair of jeans and his favorite flannel, his hair is clean, soft, and a little more fluffy than usual, and he feels as ready as he’ll ever be. Except that he was worried about talking to Gabe. Like the emotionally compromised moose he’s always been, he made the moronic decision to turn off his phone. Because, you know, avoiding problems is just how he rolls. Ugh. 

He glances at his watch, sees it’s already 6, grabs his keys, and runs out the door. It’ll take a solid thirty minutes to get to the Roadhouse, a small diner/bar in town that basically all the locals had been to at one point or another. Sam himself wasn’t a huge fan because all the food there was greasy and gave him stomach aches (and probably artery blockages, though he couldn’t prove that until he actually had a heart attack). 

He hops into his car and zooms out of the apartment complex’s small parking lot. Speeding isn’t necessary yet, but he wants to be ready for that eventuality, just in case traffic is bad or something. Not that being late is the worst thing in the world… Oh screw it, Sam fucking hates being late. He hates being early too, actually. If only he were a wizard, then he wouldn’t have to deal with either. 

The drive is pretty uneventful. Sam yells at someone who doesn’t use their blinker when turning and rolls his eyes when he sees someone with a bumper sticker supporting a certain asshole politician, but other than that, it’s smooth sailing. Or, driving, rather.

He finally arrives, at 6:30 on the dot, and makes his way inside. (He’s definitely hoping someone is already here, because he hates being the first person somewhere and having to find a table and wait for everyone else. Jesus, first world problems.)

Fortunately, he spots Dean chatting it up with a young woman at the bar, so he makes his way over to his brother and greets him with a pat on the back.

“Oh, hey Sammy.” Dean smiles, then realizes Sam has no fucking clue who the random woman standing there, staring at him is, so he continues, “This is Jo, Sam. Her mom owns the place, and she helps me out at the garage sometimes.”

They had better not be in a fucking relationship, or Sam will cut this bitch. Not really. In fact, he’d love to see Dean happy, no matter who he’s with, but still, it would really suck for Cas.

“So, you two together...?” He crosses his mental fingers as he offers the question, and is very relieved at the response it’s met with. Namely, an eye roll from Dean, an overacted gagging motion from Jo, and a resounding “No way, ew,” from both of them. 

They chat for a couple minutes before Sam suggests they go sit down at a booth and wait for his friends to get there. Jo smacks Dean lovingly on the back of the head as they walk off, and Sam grin. He’s honestly so glad Dean has friends here in town. Growing up, moving around so much, Dean had never really made many friends. They’d never stayed at one school long enough for an introverted guy like his older brother to actually form any real relationships, and Sam is realizing now that he’s never really seen Dean interact with someone he was close to other than family. (Uncle Bobby is family, and fuck anyone who says otherwise.)

They don’t have to wait long before Sam spots two lost-looking Novaks over Dean’s shoulder as they stumble in the front door, and he waves them to come over. 

Gabe looks tired and… worried? Why does he look worried? Anyway. Cas looks confused, and their eyes are their constant squinty selves. 

“Hey guys, glad you could make it,” Sam smiles as he greets his friend and boyfriend, and Dean twists around to see the newcomers. 

“Wait, Cas??” Dean sounds so damn confused, and it’s hilarious. 

Sam watches Cas’ face as comprehension dawns, and he and Gabe share a small laugh, gleefully watching their respective brothers. Gabe sits down next to Sam, and they wait as Cas slowly makes their way over to sit next to Dean. 

“Oh, so you know each other?” Sam tries to sound as surprised as possible, but Gabe snorts a laugh, and Sam knows he can’t hold onto his straight face for much longer. Oh dear, the plan is probably going straight out the window if this is only the start of the evening. 

Dean is the first of the pair to respond to Sam’s question. “Uh, yeah, Cas and I are friends. Roommates, actually.”  
Sam leans over to Gabe and whispers, “And they were roommates!” And of course, Gabe grins and whispers back, “Oh my god, they were roommates.” 

There’s a bit of a lull in conversation where Sam and Gabe are excitedly watching Cas and Dean, Cas is nervously fiddling with their trademark blue tie (do they ever change clothes?), and Dean is chewing the inside of his cheek and tapping his fingers lightly on the table. Exciting stuff, to be sure. 

Before Sam can interject something into the painful silence, Gabe taps his shoulder softly, and murmurs, “Hey, can I talk to you in private, Sam?”

Ohhhhh, Sam suddenly remembers what all the commotion had been so pleasantly distracting him from: the love situation. And now Gabe wants to talk to him in private. Break up with him in private. Murder him in private? 

“Will you guys excuse us for a minute?” Sam smiles apologetically at Cas and Dean, then let Gabe lead him away to the bathroom. Because where better to have a serious discussion?

As soon as the door is shut, Gabe whirls around, and Sam is taken aback by the seriousness in his tone as he says, “What the fuck, man?!” 

Yep, this is it. Gabe can’t fucking fathom why Sam said he loved him, and now there’s hell to pay. “Look, I’m sorry, I really am…” He trails off and fidgets quietly, avoiding Gabe’s eyes.

He’s surprised however by a comforting, out of the blue hug. He melts into it, not realizing that he was actually super fucking tense. A few good back rubs, and Gabe pulls back.

“Okay, now let’s try again,” he crosses his arms, though not in the judgemental way Sam would have expected, but with a calm, curious expression in his eyes. “So spill, Sammoose. Why wouldn’t you get back to me last night or today? I was really damn worried.”

Ugh, of course he was worried! Sam had been such an idiot! Gabe is a sweetheart, and Sam had turned off his phone after hanging up on him. He was probably worried about Sam’s safety or something. Great going, Sam.

“I’m really sorry, Gabe. I wasn’t thinking. I mean, like, the words just accidentally slipped out, and then I was so worried you were going to like hate me for it, you know? So, yeah. I’m really sorry.” Nice, all that in one breath. 

“Well, I guess that sort of makes sense. But Jesus, Sam. Can you not do that again?” Gabe runs a hand through his hair with a sigh, and Sam feels a fucking wet comforter of guilt land on him. Yes, a wet comforter. It’s awful.

“Of course, man. Honestly, I was just so embarrassed. I mean, we’ve been seeing each other for such a short amount of time, I just said it out of habit, and then I felt so stupid afterwards.” Sam talks really quickly when he’s uncomfortable. Fun fact.

Gabe pauses for a second and quirks an eyebrow. “Now, I might just regret asking this, Sam-o. But… I’m guessing that means you don’t love me?”

Oh shit, Sam didn’t mean it like that. Um, shit. “Uh, well, I mean. Maybe? It’s not that I…” Sam trails off, because how the fuck does he answer this?

Gabe jumps in with a probably fake grin. “Don’t give yourself an aneurysm, I get it. It’s all right, I was just wondering.”

Yeah, Gabe looks sadder. This is not the perfect situation. Damn it, why does Sam have to suck at dealing with emotional things? 

“Look, I mean, I guess I just don’t know yet, you know?” He channels all his years of staring at people’s heads are trying (unsuccessfully) to mind control them or send them a subliminal message into one giant force of will to make Gabe understand and still like him.

Apparently it works, because Gabe actually, genuinely smiles up at him and responds, “Of course I understand, Sam. Hell, we’ve only known each other for a couple months.”

“Exactly! Like, I really like you! And I might love you! I just don’t know yet. I want to know you better. I mean, like, I can say that I _philia_ you, and I _storge_ you, and I might _eros_ you, and maybe on some level I _agape_ you…” Same trails off again, because wow, nerd alert. 

His nerdom is confirmed as Gabe pushes up to his tiptoes, kisses him softly, and whispers, “You read too much,” into his mouth. 

“That’s sexy,” Sam deadpans. 

Okay, so, it’s all right. They’re all right with not for sure being in love for now, Gabe doesn’t hate Sam, and Sam probably reads too much. All is right with the world. So… why were they here this evening?

“Oh Jesus, we left Cas and Dean out there, didn’t we?” Gabe groans and lets his forehead fall onto Sam’s chest (which does NOT make Sam freak out, because oh my god Gabe’s face is touching his chest; nope, definitely not). 

They take a minute to gather themselves, grab each other’s hands, and exit the bathroom. Sam actually feels himself blush (which hardly ever happens in real life) as he notices there’s a small line for the bathroom. Oh shit, it looks like they were having sex in there, doesn’t it? He glances down at Gabe, and as if to confirm his suspicions, Gabe is smirking widely and walking with an extra bounce in his step. 

They get back to the booth and are met by a matching pair of disgusted faces. 

“Jeez Sammy, you know they never clean that bathroom, right? I mean, it’s gotta be STD central in there…” 

Sam gives his brother his iciest bitchface. “We were not--”

“Yeah, that’s what I tried to tell him, but little Sammy here just can’t keep it in his pants!” Gabe cuts in with a laugh and a playful elbow to Sam’s side. 

Sam turns to his boyfriend slowly and meticulously. He makes sure he holds his eyes as he says, “I no longer _storge_ you, and that _eros_ is a lot further off.”

Cas giggles. Wait, did Cas just giggle? That’s weird. Anyway. Weird fucking night, and it’s only just getting started. Lord help him, Sam will have lost a few years to stress by the end of the night.

**Notes for the Chapter:**

> Wowow, what's going to happen next?! (I certainly don't know, so please tell me, so I can steal your ideas. Haha, just kidding. ...probably.)
> 
> Anyway, I hope you liked this chapter! Let me know what you thought? I philia and storge all of you ^_^


	9. Fuck Alliteration, Shit's Going Down (Part II)

**Notes for the Chapter:**

> First of all, thank you guys so much for all the support on my last chapter!!  
> Second of all, if you want to check it out, I made a cover photo for this fic, and it's in the first chapter now (I actually really like it...eheheheh)  
> Third of all, I'm planning on making this into a series! I'm going to put a little more info about my plans for it in the notes at the end of the chapter.
> 
> And fourth of all. I'M SO SORRY IT TOOK SO LONG FOR THIS CHAPTER TO COME OUT AHFLKJAEFKASJFHASLKJFHASKJFDD

So yeah. Cas just giggled like a… Well, the only phrase coming to Sam’s mind is ‘giggly bitch,’ but that doesn’t really fit the situation, so Sam decides to move on. He scowls at Dean’s smug face, then turns to Gabe and scowls at him too. 

“Oh come on, Sammoose,” Gabe grins, which definitely does _not_ melt a little of Sam’s heart, and then leans up on his tiptoes to plant a small kiss on Sam’s grimacing mouth. 

Ugh, why is Sam such a pushover? He honestly can’t help it; he has a heart of butter (though, he likes to pretend he’s a stone cold bitch), and he really just can’t stay mad at people. Well, except maybe family members. But they’re different. Anyway. 

He reluctantly gives in as Gabe grabs his hand and pulls him down to sit opposite Dean and Cas, who are locked in conversation now and seem to be ignoring all their surroundings. 

“Aren’t they cute?” Gabe leans over and whispers into his boyfriend’s ear, earning him a snort and a nod from Sam. 

After a moment, Cas and Dean seem to notice their respective brothers’ blatant staring and go back to looking equally uncomfortable and awkward. 

Sam decides to break the silence with, “So how do you guys know each other?” Seems like an innocent question, right? Well, apparently not, because they both start blushing to high heavens, and Cas starts incoherently mumbling. 

Finally, after Sam has regretfully mulled over every single life decision that brought him to the uncomfortable situation he is currently sitting in, Dean clears his throat and begins the narrative. “Well, actually. Uh, funny story… See, Cas ‘n I met at a bar. And, well, I like to say he pulled me out of hell…” Dean peters off and rubs the back of his neck with a shy grin at Cas.

“Oh seriously Dean, just tell them what happened,” Cas elbows Dean softly, then continues staring down into his drink, as if the bubbles of the brown soda were the most fascinating thing ever. Which, they kind of were a little bit to Sam, but that’s neither here nor there.

At Cas’ nudging, Dean continues. “Well, okay. So, it was a bar. Um. It might have been, kinda, a gay bar…” Dean looks up to Sam and Gabe, as if expecting looks of shock and surprise, but he’s met with silent attentiveness and maybe a snicker from Gabe. 

“Yeah, so. I actually got dared to go there with a friend. You probably don’t know him, Sam. Name’s Crowley?” Sam shakes his head no. “Yeah, I met him after you left. Anyway, it was just weird, and I hated it, but Crowley wouldn’t fucking let me go home. I got kinda drunk, and I didn’t have a way home, and Crowley was being a real dick about it. But Cas just kinda appeared and pulled me outta there. I mean, literally. He grabbed me by the fucking arm, and it hurt. Like, I had a bruise for a couple days. The dude’s got killer grip strength...” At this point, Dean is basically just gawking at Cas as he talks, and it’s all sorts of cute. 

“So why were _you_ in there, Cassie?” Gabe grins at Cas’ scandalized expression. 

“Um…” Cas is awfully close to just dunking their entire head into their drink at this point, and Sam is feeling pretty sorry for them, so he shoots a meaningful glare at Gabe, hoping he’ll drop it.

Before Cas can actually answer (or properly look up from his drink, for that matter) Dean jumps in to his rescue. “It was almost the same thing for him, actually.” 

Suddenly, a mortified look suddenly flashes onto Dean’s face. “Wait, shit, I’m sorry Cas. I’ve been saying ‘him’ and ‘he’ and shit…”

Oh damn, Sam hadn’t even noticed. Sam kinda sucks at remembering to properly gender people too, because he grew up with a father who definitely wasn’t an ally and didn’t do shit to teach his sons about the LGBT community. Not that many parents of born when John was would… But that’s besides the point, because Dean looks so upset that he’d forgotten it’s making Sam want to cry. And he will not cry. No crying in public for at least another week. 

Cas gives Dean a warm smile and places a hand on his shoulder. “It’s fine, Dean. Don’t worry about it.”

“Nah, I _will_ worry about it, because it’s important to you, right? Yeah.” He kinda harrumphs and nods his head, causing Cas to giggle (a-fucking-gain). 

“Anyways,” Dean goes back to his story, “Cas was there with a school buddy--Balth, right?--and they didn’t want to be there any more than I did. ‘Course, they got way less drunk than me… fucking saved me from hell that night, buddy.” 

Oh fuck, the heart eyes are happening. Sam is torn between watching the almost inappropriate eye-fucking going on in front of him and looking over to touch bases with Gabe. To avoid sweetness induced vomiting, he decides on the latter option. 

“Jesus, it’s like we’re not even here…” Gabe murmurs, and Sam nods and cracks a grin.

After what feels like an eternity (Sam has a great sense of time, obviously) Dean and Cas seem to simultaneously remember their brothers and snap out of their trance-thing. 

“Um, so what about you, Sam? How’d you meet Cas?” Dean asks innocently. 

Cas is just having a rough day, honestly, because yes, that’s another embarrassing question for them. Sam snickers remembering how ridiculously awkward Cas had been the first time they had met back in June. Jesus, tons of shit had actually changed since then.  
“Uh, you wanna tell him, Cas?” Sam thinks it’d probably be best for Cas to handle this conversation, considering he has no idea how much they’re cool with Dean knowing about that first--and all subsequent--conversations. 

Cas blushes (yes, again; you can’t make this shit up, okay?) and runs a hand through their hair. 

“Well,” they’ve gone back to resolutely studying their drink, and they’re nervously fiddling with their tie as they start talking. “I was in Sam’s grocery store, and I noticed he was wearing gay pride clothing, and I myself was going through some questioning at that point about my sexuality, so I thought he’d be as good a person as any to ask about it…” Somehow, Cas managed to trail away in such a way as to make it sound like they were asking a question rather than telling a story, and Sam honestly relates.

Dean doesn’t, apparently. “Dude, what the fuck, Cas? You could have talked to me about that; I mean, I know I’m not great about remembering everything about sexuality, but I’m better than talking to a complete stranger, right?” 

Cas ducks their head and responds, “I didn’t think you’d be comfortable with it. I mean, it’s not something you really have experience with so I…”

“What?! I’m super comfortable with it! I’m attracted to guys too, you know.” 

Cas deflates, and suddenly Sam remembers one of his first conversations with them. When Cas had first found out Dean was bi, they had been heartbroken, because they thought that meant Dean wasn’t attracted to them. Now, Sam knew that was bullshit, but Cas didn’t. Shit. How can he fix this?

At this point, Dean is scowling with his arms crossed defensively and Cas looks looks like they’re definitely about to break out into tears. What the fuck happened to _the Plan_?

Gabe suddenly pipes up, mildly surprising everyone, because he’d been silent for so long. He clap his hands together with a loud huff of air, then boisterously suggests, “Let’s order!” 

It’s very obvious, at least to Sam, that Gabe has had about his fill of uncomfortable pauses in the conversation, and honestly Sam has too, so he offers an enthusiastic nod and waves at their waitress to come back. 

“Um, Jo, right? Yeah. Can I get whatever salad you have with a side of sweet potato fries?” Sam orders quickly, then gives Gabe a small back rub/pat/thing in a rather sad attempt to comfort his extroverted boyfriend. _Sam used back rub… it’s super effective!_ Jesus, he’s such a nerd.

Gabe and Cas both order, pancakes and a burger, respectively. Jo looks expectantly at Dean, and he gives her a winning smile. “I’ll have two double bacon cheeseburger, of course.” Jo rolls her eyes, and Sam gets the impression that this is some sort of standing order that Dean gets at the Roadhouse. Yikes. 

Sam is about to mention something about the dangers of such a diet for Dean’s health, particularly his heart health, which Cas speaks up. “Dean, if you keep eating like that, you’ll be dead before you hit 50.” Jesus, Cas’ demeanor has gone from sad to scary, and Sam isn’t sure he totally loves the cold, kind of asshole-ish side of his friend. 

“Yeah, well fuck you, Cas,” Dean says curtly. Okay, looks like neither Winchester likes this side of Cas very much. 

Jo saunters off with their orders, and a painful silence falls over the table. Gabe is looking more pathetically uncomfortable than Sam has ever seen him, and he realizes it’s because Cas is so uncomfortable. Gabe might be a dick, but damn if he doesn’t care about his little brother. 

Meanwhile, Cas and Dean are resolutely staring in opposite directions, each wearing matching frowns. Well, ‘frown’ is a little kind. Angry frowns. Is there a word for that? Frangry aowns. Okay, back on topic.

Sam honestly doesn’t even get why they’re so upset. Like, why the fuck does Dean care that much that Cas didn’t want to talk to him about their sexuality? So, being the smart, not at all stupid individual he is, Sam asks that very question. 

Dean is quiet for a minute, and Gabe shoots Sam a terrifying death glare. Okay, yes, Sam is maybe stupid sometimes, and he has regrets. Lots of regrets. 

Finally, Dean answers. “Look, Cas is my best friend, and he should talk to me about shit. That’s what best friends are fucking _for_.” He angles the second sentence as a stab at Cas, and Sam sees Cas’ brow furrow as he turns to face Dean straight-on.

“Oh yeah, sure, that’s what best friends are for. Well, why didn’t you tell me about your sexuality sooner? If that’s what best friends are for?!” 

“I didn’t tell you because I was worried, okay? And fuck, we weren’t even that close until more recently.”

“So why can’t you accept the same answer from me? I was really fucking worried about how you’d respond, and now here you are attacking me for a decision I made months ago, so can you really blame me?” 

Dean pauses for a second, the severity of that stab sinking in. Sam knows how low Dean’s self esteem is, and he’s sure Cas knows too. 

More subdued now, Dean looks directly at Cas and calmly utters two words: “But why?”

Cas is quieter now, too. “Why what?”

“Why were you worried? I’ve known about you sexuality for almost as long as I’ve known you. Why would you be worried to talk to me about it?” 

“Because…” Cas pauses, then sighs. “You wouldn’t understand.” 

Dean frowns (not angrily this time), then says, “Try me.” 

Cas gathers himself for a minute, and Sam suddenly realizes that this is really nothing like the Plan. He gets the feeling Cas is about to say something about being attracted to Dean, and he wonders if maybe he and Gabe should just excuse themselves to the bathroom again-- _notforsexshutup_ \-- but before he can mention it to Gabe, Cas’ dam bursts.

“Look, I love you, okay Dean? Is that what you wanted to hear? You wanted to make me say it?!” They shove their face into their hands, and a stunned silence falls over the group.

Said silence is interrupted by Gabe shouting, “Food’s here!” as he sees Jo inching away from their table. She turns red when she realizes Gabe had noticed her listening in on the conversation, and she quickly drops off their food before sneaking away.

“You… love me?” Dean asks quietly, without looking anywhere near Cas.

Suddenly, Cas’ face falls. It’s like their asshole side disappears and is replaced by their timid, awkward, anxious self that Sam is more used to. “Shit, I’m sorry, Dean. I know you don’t think of me like that and aren’t attracted to me; I’m sorry. I never wanted to put you in this situation.” 

A confused look flashes over Dean’s features. “What the hell makes you think that?”

“I mean, you’ve never shown any interest in me, and since I know you’re bisexual and generally the kind of person who goes after what they want, I just assumed…” Cas groans and runs a hand through their hair yet again.

“Look, no offense, but that’s bullshit. First of all, you’ve never given me any reason to think you would possibly be interested in me--” Sam rolls his eyes so hard he’s slightly worried the sheer eye-rolling force may cause him some sort of permanent brain damage.”--and also, why does it have to be all on me to make the first move? I’m pretty fucking new to dating guys, and I know you aren’t technically a guy, but you look like one, so you know, maybe you could make the first move on a newbie like me?”

“Children, calm down,” Gabe seems to have regained his normal, obnoxiously animated personality as he chimes into the conversation again. “You idiots seem to be overlooking the most important part of this whole stupid argument!”

Both Dean and Cas regard Gabe with similar confusion. 

His boyfriend turns to Sam with a grin and says, “Care to fill them in, sweetcheeks?”

“Only if you promise to never call me ‘sweet cheeks’ again,” Sam rubs his eyes, then turns back to the couple in question.

“If I’m not mistaken, Gabe is referencing the fact that you’ve both admitted you’re into each other, so it doesn’t matter who said it first or who was more awkward and scared than the other, because now it’s out in the open, and you can be partners like normal people without all the damn drama.” He stops for a second, considers the consequences of what he’s about to say, then says it anyway. “Cas, you can beat me up for saying this later, but I think you’ll thank me in the long run. Dean, the real reason Cas talked to me back in June was to ask me advice on how to tell if his best friend liked him. You. He liked you. Back then. Um, yeah. Anway.” 

Sam is honestly getting really tired. They haven’t even been out for all that long, but all this drama is exhausting. He watches as Dean and Cas turn to each other, eyes full of hope and love and all that shit, then he turns to Gabe. “I’m tired, can we go home?” 

Gabe shushes him at first, then notices he’s actually serious about it and gives him a sweet smile. 

“Well, we’re going to leave you two lovebirds to it,” Gabe tries to get their attention, but fails because they’re a little too caught up in each others’ eyes to pay their brothers any attention. Figures. 

Sam leaves a ten dollar bill on the table before they scamper out of the restaurant. It’s surprisingly chilly outside, and he and Gabe walk quickly to Sam’s car. 

“Want a ride home?” Sam smiles at Gabe who’s pulling his jacket tighter around his body as if that would make him warmer.

“Nah, I’ll just take my car. If Cas wants to come home tonight, Dean can drive him. Something tells me they may just both stay at Dean’s place, though…” He grins mischievously and grimaces. 

“Gross, that’s my brother you’re talking about, asshat.” 

Gabe just laughs, then raises up on his tiptoes to give Sam a soft, warm kiss. 

Sam finally grins too. “We fucking did it. We made them admit they’re in love with each other.”

Gabe quirks an eyebrow. “Um, Samsquatch, I hate to break it to you, but that definitely did not go well. Yes, they’re gonna be fucking like rabbits soon, but jesus, that was rough.”

“Yeah, I know. But I mean, it worked out, right? And all they said was just shit that had been festering for ages. It was probably good for them to get it all out of their systems; now they’re starting their relationship with clean slates.”

Gabe smiles, then suddenly smashes his face into Sam’s chest. 

“Dude, what the fuck?” Sam can feel that Gabe is saying something, but it’s way too muffled to make out. “What did you say?”

Gab pulls back fucking finally, and he’s grinning when he responds, “I _said_ , I love you, you moron.” 

Sam widens his eyes and smiles nervously at his boyfriend. “I thought we had agreed we weren’t using the non-lesbian L-word until we’d known each other for longer…?” 

“Look, you don’t have to say it back, but I fucking know already, so let me tell my hot mess for a boyfriend that I love him, okay?” Something about the way Gabe looks up at Sam sets off something in his chest that feels way too warm and fuzzy, and he feels tears pricking at his eyes.

“Ugh, fuck it, I love you too.”

**Notes for the Chapter:**

> Holy shit, it's over!!! Did you guys like it?!? Thank you all so much for reading, giving kudos and comments, and putting up with my stupid shit! Y'all are the best <3
> 
> I'm thinking I'll make two sister fics, one from Cas' POV (that takes place at the same time as this one does) and then a second fic that is basically just a long ass epilogue that'll switch POVs! (That one will probs be rated E, because there will be established relationships to write into sexy situations!!


End file.
